Welcome to LookChem.com Sign In|Join Free

CAS

  • or

104-92-7

Post Buying Request

104-92-7 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

104-92-7 Usage

Chemical Properties

colourless liquid

Uses

4-Bromoanisole finds application as an intermediate in synthetic chemistry. It is used in the preparation of aryl 1,3-diketones and ethyl 4-methoxycinnamate. It is a used as a brominating reagent. Further, it is used in Suzuki coupling reaction with phenylboronic acid as well as in Heck reaction.

Definition

ChEBI: A monomethoxybenzene carrying a bromo substituent at position 4.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7429, 1994 DOI: 10.1016/0040-4039(94)85333-9Synthesis, p. 868, 1986 DOI: 10.1055/s-1986-31813

General Description

4-Bromoanisole is a useful brominating reagent. It is formed as reaction product in the reaction between HOBr and anisole. Suzuki coupling of 4-bromoanisole with phenylboronic acid catalyzed by palladium pincer complexes has been studied. Heck Reaction of 4-bromoanisole with ethyl acrylates in room-temperature ionic liquids is reported to afford ethyl 4-methoxycinnamate.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic vapors of Br-.

Purification Methods

Crystallise the anisole by repeated partial freezing, then distil it under reduced pressure. [Beilstein 6 III 741, 6 IV 1044.]

Check Digit Verification of cas no

The CAS Registry Mumber 104-92-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 104-92:
(5*1)+(4*0)+(3*4)+(2*9)+(1*2)=37
37 % 10 = 7
So 104-92-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

104-92-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A11824)  4-Bromoanisole, 99%   

  • 104-92-7

  • 100g

  • 331.0CNY

  • Detail
  • Alfa Aesar

  • (A11824)  4-Bromoanisole, 99%   

  • 104-92-7

  • 500g

  • 1265.0CNY

  • Detail
  • Alfa Aesar

  • (A11824)  4-Bromoanisole, 99%   

  • 104-92-7

  • 2500g

  • 5329.0CNY

  • Detail

104-92-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-bromoanisole

1.2 Other means of identification

Product number -
Other names Benzene, 1-bromo-4-methoxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-92-7 SDS

104-92-7Synthetic route

methoxybenzene
100-66-3

methoxybenzene

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 3.5h; Heating;100%
With Selectfluor; sodium bromide In acetonitrile at 20℃; for 21h;100%
With bis[1-methyl-3-(3-sulfopropyl)imidazolium] hexafluorotitanate; dihydrogen peroxide; sodium bromide In water at 25℃; for 3h; Reagent/catalyst; Concentration; Solvent; Temperature; Green chemistry;100%
4-bromo-phenol
106-41-2

4-bromo-phenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 160℃; for 2h; Microwave irradiation; Green chemistry;100%
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction;95%
With magnesium oxide In N,N-dimethyl-formamide at 170℃; for 0.5h; Microwave irradiation; Green chemistry;95%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.166667h;100%
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h;96%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;85%
With N-Bromosuccinimide In acetonitrile at 81℃; for 1.5h;82%
With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20h;70%
4,4'-dimethoxy-diphenyliodonium bromide
19231-06-2

4,4'-dimethoxy-diphenyliodonium bromide

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
In benzene-d6 at 120℃; for 5h; Sealed tube;100%
rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene In 2,2,2-trifluoroethanol at 20℃; for 0.166667h; regiospecific reaction;100%
4-bromo-phenol
106-41-2

4-bromo-phenol

dimethyl sulfate
77-78-1

dimethyl sulfate

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With potassium carbonate In diethyl ether; acetone99.5%
Stage #1: 4-bromo-phenol With potassium carbonate In acetone for 0.25h;
Stage #2: dimethyl sulfate In acetone for 12h; Reflux;
95%
With aluminum oxide; potassium hydroxide for 6h; microwave irradiation;87%
With sodium hydroxide In diethyl ether for 2h; Heating;59%
methoxybenzene
100-66-3

methoxybenzene

A

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

B

2-bromoanisole
578-57-4

2-bromoanisole

C

2,4-dibromoanisole
21702-84-1

2,4-dibromoanisole

Conditions
ConditionsYield
With bromine; tetramethylammonium bromide In liquid sulphur dioxide at -23℃; Rate constant; Product distribution; Thermodynamic data; in H2O at 25 deg C, NaBr, HClO4; ΔH (excit), -ΔS (excit);A 98.99%
B 0.56%
C 0.43%
With (CH3)4Br In liquid sulphur dioxide at -23℃; Kinetics; Thermodynamic data; Product distribution; ΔH(excit.); ΔS(excit.);A 98.99%
B 0.56%
C 0.43%
With (CH3)4Br In liquid sulphur dioxide at -23℃;A 98.99%
B 0.56%
C 0.43%
4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With potassium phosphate; tetrabuthylammonium tribromide In acetonitrile at 100℃; for 16h;98%
With 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; 2,2’-disulfanediyldipyridine-1-oxide 2.) 100 deg C; Yield given. Multistep reaction;
With potassium phosphate; tetra-N-butylammonium tribromide In acetonitrile at 100℃; for 16h;
dimethyl sulfate
77-78-1

dimethyl sulfate

Amberlite IRA-400 p-bromophenoxide anion

Amberlite IRA-400 p-bromophenoxide anion

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
In methanol for 0.4h; Methylation;98%
methoxybenzene
100-66-3

methoxybenzene

A

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

B

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

Conditions
ConditionsYield
With sodium chlorite; silica gel; manganese(III) acetylacetonate; sodium bromide In dichloromethane at 25℃; for 2h;A 97%
B 3%
With tetraethylammonium chloride; tetraethylammonium bromide Product distribution; 1.) CH2Cl2, RT, 1 h, electrolysis, 2.) CH2Cl2, RT, 24 h; other halogenating agents; other benzene derivatives and olefins;
methoxybenzene
100-66-3

methoxybenzene

A

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

B

2-bromoanisole
578-57-4

2-bromoanisole

Conditions
ConditionsYield
With Oxone; potassium bromide In methanol at 20℃; for 1h;A 97%
B 2%
With Oxone; potassium bromide In acetonitrile at 20℃; for 24h;A 84%
B 15%
With PyHBrCl2 In methanol at 20℃; for 0.0833333h;A 78%
B 18%
4-methoxybenzenediazonium tetrafluoroborate
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;97%
With dibenzo-18-crown-6; N,N,N,N,-tetramethylethylenediamine; potassium bromide; copper(I) bromide; copper(ll) bromide In acetonitrile at 20℃; for 1h; Sandmeyer Reaction;90%
With potassium bromide In acetonitrile at 20℃; for 1h; Sandmeyer Reaction; Inert atmosphere;87%
With (triphenylphosphine)gold(I) chloride; sodium bromide In acetonitrile at 50℃; for 5h; Sandmeyer Reaction;67 %Chromat.
With Bromotrichloromethane; tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 20℃; for 2h; Sandmeyer Reaction; Electrochemical reaction;55 %Chromat.
4-bromo-phenol
106-41-2

4-bromo-phenol

methyl iodide
74-88-4

methyl iodide

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
Stage #1: 4-bromo-phenol With potassium carbonate In acetone for 0.166667h;
Stage #2: methyl iodide In acetone for 16h; Reflux;
95%
With potassium carbonate In acetonitrile at 20 - 50℃; for 6h;84%
With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;83%
(p-methoxyphenyl)tri-n-butylstannane
70744-47-7

(p-methoxyphenyl)tri-n-butylstannane

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With hydrogenchloride; chloroamine-T; sodium bromide In ethanol; water at 0℃; for 0.25h;95%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
171364-79-7

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 14h;95%
2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
171364-79-7

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 14h;95%
potassium 4-(methoxy)phenyltrifluoroborate

potassium 4-(methoxy)phenyltrifluoroborate

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;94%
4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene In 2,2,2-trifluoroethanol at 20℃; for 0.166667h; Solvent; regiospecific reaction;91%
With bis(collidine)bromine(I) hexafluorophosphate In dichloromethane at 20℃; for 3h;70%
2-(4-methoxy-phenyl)-decan-2-ol

2-(4-methoxy-phenyl)-decan-2-ol

A

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

B

Decan-2-one
693-54-9

Decan-2-one

Conditions
ConditionsYield
With bis(collidine)bromine(I) hexafluorophosphate In dichloromethane at 20℃; for 1.5h;A n/a
B 91%
4-bromo-phenol
106-41-2

4-bromo-phenol

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 0.5h; Microwave irradiation;89%
t-butyldimethylsilyl-4-bromophenol
67963-68-2

t-butyldimethylsilyl-4-bromophenol

methyl iodide
74-88-4

methyl iodide

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide for 12h; Ambient temperature;88%
4-bromo-phenol
106-41-2

4-bromo-phenol

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With boron trifluoride In diethyl ether for 0.0333333h; microwave irradiation;86%
sodium methylate
124-41-4

sodium methylate

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
In methanol Product distribution; Heating;85%
In methanol at 110℃; for 0.5h;85%
triethyl(4-methoxyphenyl)germane

triethyl(4-methoxyphenyl)germane

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h;85%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
Stage #1: 4-methoxy-aniline With Bromotrichloromethane; sodium nitrite In dichloromethane; water at 23℃; for 0.0833333h; Sealed tube;
Stage #2: With acetic acid In dichloromethane; water at 70℃; for 24h; Temperature; Sealed tube;
84%
With N-Bromosuccinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6h;80%
Stage #1: 4-methoxy-aniline With boron trifluoride diethyl etherate; lithium bromide In acetonitrile at 0℃; for 0.166667h;
Stage #2: With tert.-butylnitrite In acetonitrile at 0 - 20℃; for 1h;
80%
4-bromophenyl acetate
1927-95-3

4-bromophenyl acetate

methyl iodide
74-88-4

methyl iodide

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide for 0.5h; Ambient temperature;84%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

methyl iodide
74-88-4

methyl iodide

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
Stage #1: 1,4-bromoiodobenzene With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In water; dimethyl sulfoxide at 20 - 100℃; Inert atmosphere;
Stage #2: methyl iodide With tetra-(n-butyl)ammonium iodide; potassium hydroxide In water; dimethyl sulfoxide at 20 - 100℃; Inert atmosphere;
84%
1,1-bis-(4-methoxy-phenyl)-pentan-1-ol

1,1-bis-(4-methoxy-phenyl)-pentan-1-ol

A

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

B

p-Methoxyvalerophenon
1671-76-7

p-Methoxyvalerophenon

Conditions
ConditionsYield
With bis(collidine)bromine(I) hexafluorophosphate In dichloromethane at 20℃; for 1.5h;A n/a
B 83%
4-bromo-phenol
106-41-2

4-bromo-phenol

trifluoroacetic acid-methyl ester
431-47-0

trifluoroacetic acid-methyl ester

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
Stage #1: 4-bromo-phenol With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: trifluoroacetic acid-methyl ester In N,N-dimethyl-formamide for 10h;
83%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

(4-D)-Anisol
20938-43-6

(4-D)-Anisol

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: With d(4)-methanol In tetrahydrofuran at -78 - 0℃; Inert atmosphere;
100%
With tetrahydrofuran-d8; 2,2'-azobis-(2,4-dimethylvaleronitrile); tri-n-butyl-tin hydride for 5h; Reflux; regioselective reaction;94%
With sodium amalgam; deuteromethanol for 2h; Heating;90%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

4-bromo-2-iodo-anisole
98273-59-7

4-bromo-2-iodo-anisole

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene In tetrahydrofuran; hexane; pentane at -30℃; for 20h;
Stage #2: With iodine In tetrahydrofuran; hexane; pentane at 20℃; for 1h; Further stages.;
100%
With iodine; 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one In acetonitrile for 16h; Ambient temperature;99%
With [bis(acetoxy)iodo]benzene; iodine In ethyl acetate at 60℃; for 5h;99%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

4-trimethylsilylanisole
877-68-9

4-trimethylsilylanisole

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere;100%
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃;
99%
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 18h; Inert atmosphere; Schlenk technique;
96%
styrene
292638-84-7

styrene

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

p-methoxystilbene
1694-19-5

p-methoxystilbene

Conditions
ConditionsYield
With cis-(N,N'-bis(2,2-diethoxyethyl)imidazolin-2-ylidene)dichlorotriphenylphosphinepalladium(II); tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 2h; Heck reaction;100%
With 1-naphthalenomethyl-3-benzylimidazolidinium chloride; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 2h; Reagent/catalyst; Green chemistry;100%
With C180H144O4P8Pd4S4(4+)*4CF3O3S(1-); sodium acetate In N,N-dimethyl acetamide; water at 120℃; for 24h; Solvent; Reagent/catalyst; Temperature; Heck Reaction; Inert atmosphere;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

4'-methoxy-2-methylbiphenyl
92495-54-0

4'-methoxy-2-methylbiphenyl

Conditions
ConditionsYield
With C31H26N6O4Pd; potassium carbonate In water at 100℃; for 3h; Suzuki-Miyaura coupling;100%
With C38H53Cl2N2O2PPd*CH2Cl2; tetrabutylammomium bromide; potassium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique;100%
With potassium phosphate; (PdCl2)(2-pyridyl)-6-isopropyl cis piperidine complex In water; N,N-dimethyl-formamide at 110℃; for 2h;99%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone
75467-36-6

5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone

5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-1-C-(4-methoxyphenyl)-D-ribofuranose
115129-94-7, 115130-17-1

5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-1-C-(4-methoxyphenyl)-D-ribofuranose

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; pentane 1.) -78 to 0 deg C, 1 h, 2) -78 deg C, 6 h;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

para-iodoanisole
696-62-8

para-iodoanisole

Conditions
ConditionsYield
With copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane for 24h; Reflux;100%
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide In acetonitrile at 100℃; for 1.25h; Buchwald's halogen exchange reaction; Inert atmosphere; Microwave irradiation;95%
With copper(I) oxide; L-proline; potassium iodide In ethanol at 110℃; for 30h; Schlenk technique; Inert atmosphere; Sealed tube;87%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2,4-dibromoanisole
21702-84-1

2,4-dibromoanisole

Conditions
ConditionsYield
With (CH3)4Br In liquid sulphur dioxide at -23℃; Rate constant;100%
With (CH3)4Br In liquid sulphur dioxide at -23℃;100%
With N-Bromosuccinimide; iodine In acetonitrile for 12h; Darkness;93%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With hydrogen In methanol at 70℃; under 750.075 Torr; for 0.333333h;100%
With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;98%
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -58℃; for 0.000861111h;
Stage #2: With methanol In tetrahydrofuran; hexane at -58℃; for 0.000436111h;
92%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

phenylacetylene
536-74-3

phenylacetylene

4-(phenylethynyl)anisole
7380-78-1

4-(phenylethynyl)anisole

Conditions
ConditionsYield
With copper(l) iodide; 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 130℃; for 20h; Sonogashira cross-coupling;100%
With copper(l) iodide; ethanolamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water at 60℃; for 24h; Sonogashira coupling;99%
With copper(l) iodide; triethylamine; tris(dibenzylideneacetone)dipalladium (0) In toluene at 20℃; Sonogashira coupling;98%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

phenylboronic acid
98-80-6

phenylboronic acid

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 14h; Suzuki-Miyaura cross-coupling reaction;100%
With 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling;100%
With 1,4-diaza-bicyclo[2.2.2]octane; PEG-400; potassium carbonate; palladium diacetate at 110℃; for 2h; Suzuki-Miyaura cross-coupling reaction;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

(E)-3-(4-methoxyphenyl)acrylic acid butyl ester
173464-57-8, 40458-52-4, 121725-19-7

(E)-3-(4-methoxyphenyl)acrylic acid butyl ester

Conditions
ConditionsYield
With 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 130℃; for 20h; Heck cross-coupling;100%
With phenyl carbamate; tetrabutylammomium bromide; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 130℃; for 2h; Heck-type reaction;99%
With potassium carbonate; di-μ-acetato-bis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]dipalladium In ISOPROPYLAMIDE99.2%
styrene
292638-84-7

styrene

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

E-1-(phenyl)-2-(4'-methoxyphenyl)ethene
1694-19-5

E-1-(phenyl)-2-(4'-methoxyphenyl)ethene

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate In N,N-dimethyl acetamide at 140℃; for 42h; Heck reaction;100%
With 1,3-bis-(2-ethoxybenzyl)-3,4,5,6-tetrahydropyrimidinium chloride; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 4h; Heck reaction; stereoselective reaction;99%
With C34H26Cl2N10Pd; tetrabutylammomium bromide; sodium acetate at 120℃; for 12h; Reagent/catalyst; Heck Reaction;99%
morpholine
110-91-8

morpholine

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

N-(4-methoxyphenyl)morpholine
27347-14-4

N-(4-methoxyphenyl)morpholine

Conditions
ConditionsYield
With (55)Pd068(44)Ni032; potassium carbonate In water at 50℃; for 5h; Catalytic behavior; Buchwald-Hartwig Coupling;100%
With sodium t-butanolate; 1-(2-di-tert-butylphosphinophenyl)-3,5-diphenyl-1H-pyrazole; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol at 85℃;99%
With potassium hydroxide; bis(tri-tert-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 3h;99%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

acetophenone
98-86-2

acetophenone

2-(4-methoxyphenyl)acetophenone
24845-40-7

2-(4-methoxyphenyl)acetophenone

Conditions
ConditionsYield
With [(di-tert-butylneopentylphosphine)PdCl2]2; sodium t-butanolate In toluene at 22℃; for 5h; Inert atmosphere;100%
With C16H14N6O4Pd; potassium tert-butylate In acetonitrile at 82℃; for 2h; Schlenk technique; Reflux;93%
With sodium t-butanolate; palladium diacetate; 2'-hydroxy-2-di-cyclohexylphosphinobiphenyl-4'-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 14.75h;82%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

tributylphenylstannane
960-16-7

tributylphenylstannane

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With 1,1-Dimethylurea; ammonium chloride; LACTOSE; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane at 90℃; for 6h; Stille coupling;100%
With cesium fluoride; palladium(II) trifluoroacetate In 1,4-dioxane at 100℃; for 6h; Stille cross-coupling;99%
With potassium fluoride; tetrabutylammomium bromide; tris-(o-tolyl)phosphine; copper(I) oxide at 125 - 130℃; for 30h; Stille cross-coupling;96%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

1,2-dimethyl-5-(4-methoxyphenyl)-1H-imidazole

1,2-dimethyl-5-(4-methoxyphenyl)-1H-imidazole

Conditions
ConditionsYield
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere;100%
With palladium diacetate; potassium carbonate; tricyclohexylphosphine; Trimethylacetic acid In N,N-dimethyl-formamide at 180℃; for 0.5h; Inert atmosphere; Microwave irradiation;85%
With C24H22ClN3OPdSe; potassium carbonate; Trimethylacetic acid In dimethyl amine at 110℃; for 10h; Reagent/catalyst; regioselective reaction;84%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

p-toluidine
106-49-0

p-toluidine

N-(4-methylphenyl)-4-methoxyaniline
39253-43-5

N-(4-methylphenyl)-4-methoxyaniline

Conditions
ConditionsYield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate In water at 20℃; Temperature; Buchwald-Hartwig Coupling; Inert atmosphere;100%
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate In water at 20℃; for 21h; Inert atmosphere; Micellar solution;99%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 110℃; for 144h; Buchwald-Hartwig amination;97%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

4-(4-tolyl)anisole
53040-92-9

4-(4-tolyl)anisole

Conditions
ConditionsYield
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.166667h; Suzuki-Miyaura reaction;100%
With sodium carbonate; polystyrene-supported N-heterocyclic carbene-Pd catalyst In N,N-dimethyl-formamide at 20℃; for 24h; Suzuki reaction;99%
With C28H38Cl2N2O6PdS2(2-)*2Na(1+); potassium carbonate In ethanol; water at 70℃; for 1.5h; Suzuki coupling;99%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

2-(4-methoxyphenyl)-1-phenylpropan-1-one
35572-38-4, 35572-40-8, 84839-92-9, 35572-39-5

2-(4-methoxyphenyl)-1-phenylpropan-1-one

Conditions
ConditionsYield
With [(di-tert-butylneopentylphosphine)PdCl2]2; sodium t-butanolate In toluene at 22℃; for 5h; Inert atmosphere;100%
With diaminochlorophosphine ligand; sodium t-butanolate; [Pd(dibenzylideneacetone)2] In toluene at 105℃; for 24h;98%
With sodium t-butanolate; (1,1'-bis(di-tert-butylphosphino)ferrocene)PdCl2 In tetrahydrofuran at 20℃;97%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

heptanal
111-71-7

heptanal

tri-n-butyllithium magnesate complex

tri-n-butyllithium magnesate complex

1-(4-methoxyphenyl)-1-heptanol

1-(4-methoxyphenyl)-1-heptanol

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene; tri-n-butyllithium magnesate complex In tetrahydrofuran; hexane at 0℃; for 0.5h;
Stage #2: heptanal In tetrahydrofuran; hexane at -78℃; for 0.5h; Further stages.;
100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(4-methoxyphenyl)naphthalene
27331-33-5

1-(4-methoxyphenyl)naphthalene

Conditions
ConditionsYield
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water; acetonitrile at 50℃; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water; acetonitrile at 50℃; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With C38H53Cl2N2O2PPd*CH2Cl2; tetrabutylammomium bromide; potassium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4,4'-Dimethoxybiphenyl
2132-80-1

4,4'-Dimethoxybiphenyl

Conditions
ConditionsYield
With air; potassium carbonate; [Pd(Cl)κ2N,C,-CH2C6H2(4,6-Me)2CH=NC6H3(2,6-iPr)2]2 In ethanol for 2h; Suzuki-Miyaura coupling reaction; Heating;100%
With sodium carbonate; palladium on activated charcoal In ethanol at 20℃; for 5h; Suzuki-Miyaura cross-coupling;100%
With potassium carbonate In water at 50℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

4-acetylphenylboronic acid
149104-90-5

4-acetylphenylboronic acid

1-(4'-methoxy-biphenyl-4-yl)-ethanone
13021-18-6

1-(4'-methoxy-biphenyl-4-yl)-ethanone

Conditions
ConditionsYield
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 48h; Suzuki-Miyaura coupling reaction;100%
With potassium carbonate In ethanol; water at 50℃; for 2.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;98%
With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); potassium carbonate In water for 8h; Catalytic behavior; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; Reflux;97%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

phenylboronic acid
98-80-6

phenylboronic acid

A

biphenyl
92-52-4

biphenyl

B

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With potassium hydroxide In toluene at 100℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;A n/a
B 100%
With C34H28Cl2N2P2Pd(2+); potassium carbonate In isopropyl alcohol at 20℃; for 4h; Reagent/catalyst; Suzuki-Miyaura Coupling;A 3%
B 98%
With potassium carbonate In ethanol; water at 60℃; for 5h; Catalytic behavior; Suzuki-Miyaura Coupling;A 6.3%
B 87%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2,4'-dimethoxybiphenyl
49602-47-3

2,4'-dimethoxybiphenyl

Conditions
ConditionsYield
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 5h; Suzuki-Miyaura reaction;100%
With sodium hydrogencarbonate; palladium on activated charcoal In methanol at 20℃; for 8h; Suzuki-Miyaura coupling reaction;100%
With sodium phosphate dodecahydrate In isopropyl alcohol at 20℃; for 7h; Suzuki-Miyaura coupling reaction; Inert atmosphere;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2-Chloroaniline
95-51-2

2-Chloroaniline

2-chloro-N-(4-methoxyphenyl)aniline
53595-99-6

2-chloro-N-(4-methoxyphenyl)aniline

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene for 22h; Heating;100%
With sodium t-butanolate; palladium diacetate; (2,2-dimethylpropane-1,3-diyl)bis(diphenylphosphane) In 1,4-dioxane at 80℃; for 72h; Heating / reflux;73%
With C22H26Cl2NPPd; sodium t-butanolate In toluene at 110℃; for 22h; Inert atmosphere;

104-92-7Relevant articles and documents

Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide

Shibata, Ayako,Kitamoto, Sara,Fujimura, Kazuma,Hirose, Yuuka,Hamamoto, Hiromi,Nakamura, Akira,Miki, Yasuyoshi,Maegawa, Tomohiro

, p. 2275 - 2278 (2018)

We describe the dehydroxymethylbromination of alkoxybenzyl alcohol by using a hypervalent iodine reagent and lithium bromide in F 3 CCH 2 OH at room temperature. Selective monobromination or dibromination was possible by adjusting the molar ratios of hypervalent iodine reagent and lithium bromide.

Gold-catalyzed halogenation of aromatics by N-halosuccinimides

Mo, Fanyang,Yan, Jerry Mingtao,Qiu, Di,Li, Fei,Zhang, Yan,Wang, Jianbo

, p. 2028 - 2032 (2010)

(Chemical Equation Presented) Golden bromination: A highly efficient and mild AuCl3-catalyzed bromination of aromatic rings with Nbromosuccinimide (NBS) has been developed. This method works with a low catalyst loading (down to 0.01 mol %) and can be combined with transition metal catalyzed transformations to deliver various aryl products.

Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions

He, Xinxin,Wang, Xinyan,Tse, Ying-Lung (Steve),Ke, Zhihai,Yeung, Ying-Yeung

, p. 12869 - 12873 (2018)

The use of trisubstituted selenonium salts as organic Lewis acids in electrophilic halogenation and aldol-type reactions has been developed. The substrate scope is broad. The reaction conditions are mild and compatible with various functionalities. This study opens a new avenue for the development of nonmetallic Lewis acid catalysis.

-

Uemura et al.

, p. 147 (1974)

-

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ

Baik, Woonphil,Luan, Wanqiang,Lee, Hyun Joo,Yoon, Cheol Hun,Koo, Sangho,Kim, Byeong Hyo

, p. 213 - 219 (2005)

Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually 7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides.

An efficient, rapid and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst

Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish

, p. 8693 - 8697 (2006)

A simple, efficient and rapid method has been developed for high-yielding regioselective nuclear monobromination of aromatic and heteroaromatic compounds using NBS in the presence of sulfonic-acid-functionalized silica at room temperature. The catalyst works under heterogeneous conditions and can be recycled.

Solvent effect in the free-radical oxidation and electrophilic ipso and hydrogen displacement of p-methoxybenzyl alcohol and N-(p-methoxybenzyl)acetamide by Br2

Bravo, Anna,Fontana, Francesca,Dordi, Barbara,Minisci, Francesco

, p. 3880 - 3881 (2000)

-

Green halogenation reactions for (hetero)aromatic ring systems in alcohol, water, or no solvent

Kajorinne, Jessie K.,Steers, Jennifer C.M.,Merchant, Marnie E.,MacKinnon, Craig D.

, p. 1087 - 1091 (2018)

A new method of brominating aromatic and heteroaromatic ring systems is investigated. The combination of hydrobromic acid as the halogen source, hydrogen peroxide as the oxidant, and ethanol, water, or no solvent are evaluated as greener conditions than those that have been previously published. The new conditions give high yields and good regioselectivity for a variety of substrates when the ring is activated by electron-donating groups or heteroatoms. Phenols, anisole, thiophenes, and pyrrole give comparable or superior results when compared to a traditional bromination by N-bromosuccinimide in tetrahydrofuran. Other nitrogen-containing heterocycles do not react under the conditions because they are protonated and hence deactivated; similarly, substrates with electron-withdrawing groups are not brominated. The reaction is very tolerant of a variety of functional groups.

Catalytic Sandmeyer bromination

Beletskaya, Irina P.,Sigeev, Alexander S.,Peregudov, Alexander S.,Petrovskii, Pavel V.

, p. 2534 - 2538 (2007)

An efficient catalyst system for Sandmeyer bromination is proposed. Aryl bromides and dibromides can be obtained with excellent yield by this synthetic protocol. Georg Thieme Verlag Stuttgart.

Bis(sym-collidine)bromine(I) hexafluorophosphate as oxidant

Rousseau,Robin

, p. 8881 - 8885 (2000)

Primary and secondary alcohols in solution in methylene chloride are oxidised with bis(sym-collidine)bromine(I) hexafluorophosphate in good yields to the carbonyl compounds. For secondary and tertiary alcohols in which one of the substituents is a 4-methoxyphenyl group the oxidation takes place by cleavage of the phenyl-sp3 carbon bond and formation of bromoanisole and carbonyl compounds. (C) 2000 Elsevier Science Ltd.

One-pot synthesis of 4-aryl-2-aminothiazoles from styrenes and thioureas promoted by tribromoisocyanuric acid

de Andrade, Vitor S.C.,de Mattos, Marcio C.S.

, (2020)

A simple and efficient one-pot protocol has been developed for the conversion of styrenes into 4-aryl-2-aminothiazoles using readily available starting materials. Tribromoisocyanuric acid was successfully used for the co-bromination and oxidation of styrenes to give phenacyl bromides, which in the presence of thioureas produced the corresponding 4-aryl-2-aminothiazoles in 48–70% yield. The protocol involves three reactions in one process: a tandem (formation of phenacyl bromides from styrenes) followed by a telescoped (conversion to thiazole) reaction.

Brominations with Pr4NBr9 as a solid reagent with high reactivity and selectivity

Beck, Thorsten M.,Haller, Heike,Streuff, Jan,Riedel, Sebastian

, p. 740 - 747 (2014)

Tetrapropylammonium nonabromide (Pr4NBr9) is introduced as a room-temperature solid reagent for rapid bromination reactions of various substrates. The reagent exhibits reactivity similar to that of elemental bromine, but shows higher selectivity and it is easier and safer to store and to handle. Georg Thieme Verlag Stuttgart · New York.

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

Hirose, Yuuka,Yamazaki, Mirai,Nogata, Misa,Nakamura, Akira,Maegawa, Tomohiro

, p. 7405 - 7410 (2019)

We developed a mild aromatic halogenation reaction using a combination of N-halosuccinimide and PhSSiMe3 or PhSSPh. Less reactive aromatic compounds, such as methyl 4-methoxybenzoate, were brominated with PhSSiMe3 or PhSSPh and N-bromosuccinimide in high yields. No reaction was observed in the absence of PhSSiMe3 or PhSSPh. This method is also applicable to chlorination reactions using N-chlorosuccinimide and PhSSPh.

Iodine(I) reagents in hydrochloric acid-catalyzed oxidative iodination of aromatic compounds by hydrogen peroxide and iodine

Bedrac, Leon,Iskra, Jernej

, p. 1243 - 1248 (2013)

Hydrochloric acid activates the oxidative iodination of aromatic compounds with the iodine- hydrogen peroxide system through the formation of an iodine(I) compound as the iodinating reagent. Activation with hydrochloric acid is more powerful than that with sulfuric acid. The formation of dichloroiodic(I) acid (HICl2) with various forms of hydrogen peroxide was followed using UV spectroscopy. The HICl2 was used as the iodinating reagent. In the preparative oxidative iodinaton of various aromatic compounds, hydrochloric acid was used in a catalytic amount and the iodine(I) reagent was formed in situ with 0.5 equiv. hydrogen peroxide and 0.5 equiv. molecular iodine. Two types of reactivity were observed in oxidative iodination with iodine(I) species catalyzed by hydrochloric acid: in the iodination of anisole 1a better yields of iodination were observed with a smaller amount of hydrochloric acid, while on the contrary 4-tert-butyltoluene 1b gave better yields of iodination upon increasing the amount of hydrochloric acid. Reactivity was further manipulated by the choice of the solvent (MeCN, trifluoroethanol, hexafluoro-2-propanol). Copyright

Selective halogenation of aromatics by dimethyldioxirane and halogen ions

Bovicelli,Mincione,Antonioletti,Bernini,Colombari

, p. 2955 - 2963 (2001)

The oxidation of halogen anions by dimethyldioxirane (DMD) produced reactive species which led, in acidic media, to the halogenation of activated aromatic rings. The reaction can be efficiently controlled to obtain selective and mixed halogenated species.

Direct halogenation of organic compounds with halides using oxone in water - A green protocol

Firouzabadi,Iranpoor,Kazemi

, p. 1675 - 1681 (2009)

Direct bromination and iodination of various aromatic compounds with NaBr and NaI using oxone (2KHSO5·KHSO4·K 2S04) in water was accomplished successfully in high-to-excellent yields. The main benefit of this protocol is the performance of the reactions in water in the presence of a harmless oxidant without the use of any organic cosolvents. Using NaBr and NaI as the safe sources of halogens is another advantage of the protocol. This method is easily applicable to the large-scale operations. We have also applied this method successfully for the iodocyclization of an unsaturated alcohol and an unsaturated carboxylic acid.

RADICAL DECARBOXYLATIVE BROMINATION OF AROMATIC ACIDS

Barton, Derek H.R.,Lacher, Brigitte,Zard, Samir Z.

, p. 5939 - 5942 (1985)

Thiohydroxamic esters (mixed anhydrides) of aromatic and α,β-unsaturated carboxylic acids undergo clean decarboxylative bromination on treatment with bromotrichloromethane in the presence of a radical initiator.

Oxidative bromination reaction using vanadium catalyst and aluminum halide under molecular oxygen

Kikushima, Kotaro,Moriuchi, Toshiyuki,Hirao, Toshikazu

, p. 340 - 342 (2010)

The vanadium-catalyzed oxidative bromination reaction of arenes, alkenes, and alkynes was performed in the presence of AlBr3 to provide an alternative method for conventional bromination using hazardous bromine. The catalytic cycle is formed under molecular oxygen, which is more advantageous to vanadium bromoperoxidase (VBrPO) requiring hydrogen peroxide as a terminal oxidant.

An efficient regioselective NBS aromatic bromination in the presence of an ionic liquid

Pingali, Subramanya R.K.,Madhav, Monika,Jursic, Branko S.

, p. 1383 - 1385 (2010)

A simple, efficient, and rapid method was developed for high-yielding regioselective monobromination of activated aromatic compounds using NBS in combination with ionic liquid 1-butyl-1-methylimidazolium bromide ([Bmim]Br) or dioxane. The ionic liquid is recyclable and can be reused with minimal loss in the catalytic efficiency if the ionic liquid is rapidly microwaved prior to reactions.

An efficient vanadium-catalyzed bromination reaction

Moriuchi, Toshiyuki,Yamaguchi, Mitsuaki,Kikushima, Kotaro,Hirao, Toshikazu

, p. 2667 - 2670 (2007)

An efficient catalytic oxidative bromination of arenes, alkenes, and alkynes in aqueous media was achieved under relatively mild conditions by using NH4VO3 catalyst combined with H2O2, HBr, and KBr. Dodecyltrimethylammonium bromide was found to serve as an efficient surfactant to facilitate the NH4VO3-catalyzed bromination in aqueous media.

Metal- and base-free synthesis of aryl bromides from arylhydrazines

Phuc Tran, Dat,Nomoto, Akihiro,Mita, Soichiro,Dong, Chun-ping,Kodama, Shintaro,Mizuno, Takumi,Ogawa, Akiya

, (2020)

An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.

An intriguing effect of lithium perchlorate dispersed on silica gel in the bromination of aromatic compounds by N-bromosuccinimide

Bagheri, Mojtaba,Azizi, Najmedin,Saidi, Mohammad R.

, p. 146 - 149 (2005)

A convenient and efficient procedure for electrophilic aromatic bromination has been developed by mixing of N-bromosuccinimide and an aromatic compound at room temperature on the surface of silica gel mixed with solid anhydrous LiClO4. All of the substrates examined underwent clean electrophilic aromatic bromination in reaction times of a few minutes to afford the corresponding bromoarenes under neutral conditions in excellent yield. In the case of thiophenol, no substitution reaction occurred, and the corresponding disulfide was obtained in excellent yield.

The X-ray crystal structures and computational analysis of NH...π hydrogen bonded banana-shaped carbazole derivatives and thermal analysis of higher mesogenic homologues

Belloni, Maura,Manickam,Ashton, Peter R.,Kariuki, Benson M.,Preece, Jon A.,Spencer, Neil,Wilkie, John

, p. 17 - 35 (2001)

The synthesis of a series of banana-shaped mesogenic structures has been carried out, in which the bend unit is formed by the 3,6-substitution of carbazole by 4-alkoxyphenyl moieties. The crystal structures of the methoxy and propyloxy derivatives are reported with an analysis of the N-H...π interactions that are observed in the crystalline state. This analysis was aided by semi-empirical molecular orbital calculations. Additionally, the thermal analysis of the complete series has been carried out in order to investigate the phase properties of these materials. The 4-nonyloxyphenyl derivative displays two melting points by DSC and normal light microscopy, but yields non-birefringent liquids. The incorporation of photorefractive molecular units, such as carbazole. into anisotropic materials may offer many advantages over conventional electrical poling of photorefractive polymers.

Anodically-Generated Br-Cl Composite Halogenating Reagents

Fukui, Kouta,Nonaka, Tsutomu

, p. 943 - 948 (1992)

The halogenating power of Br-Cl composite species (termed "BC-reagent" in this article) generated anodically from mixtures of Br- and Cl- in CH2Cl2 was examined in an ex-cell manner toward some organic compounds.The BC-reagent brominated methoxybenzenes, and the brominating power could be precisely controlled by means of the amount of electricity charged and by varying the ratio of Cl-/Br-.The power of the reagent was less controllable during the bromination of aniline.The reaction of olefins with the BC-reagent led to dibromination and bromochlorination, the product- selectivity of which could be also controlled.The theoretically calculated chemical composition of the BC-reagent agreed fairly well with the experimentally confirmed value in some cases.

Methanolysis of 4-bromobenzenediazonium ions. Effects of acidity, [MeOH] and temperature on the formation and decomposition of diazo ethers that initiate homolytic dediazoniation

Fernandez-Alonso, Alejandra,Bravo-Diaz, Carlos

, p. 4004 - 4011 (2008)

We have investigated the effects of solvent composition, acidity and temperature on the dediazoniation of 4-bromobenzenediazonium (4BrBD) ions in MeOH-H2O mixtures by employing a combination of spectrometric and chromatographic techniques. The kinetic behaviour is quite complex; in the absence of MeOH, dediazoniations follow first-order kinetics with a half-life t1/2 ? 3000 min (T = 45 °C), but addition of small concentrations of MeOH lead to more rapid but non-first-order kinetics, suggestive of a radical mechanism, with t1/2 ? 125 min at 25% MeOH. Further increases in the MeOH concentration slow down the rate of dediazoniation and reactions progressively revert to first-order behaviour, and at percentages of MeOH higher than 90%, t1/2 ? 1080 min. Analyses of reaction mixtures by HPLC indicate that three main dediazoniation products are formed depending on the particular experimental conditions. These are 4-bromophenol (ArOH), 4-bromoanisole (ArOMe), and bromobenzene (ArH). At acidities (defined as -log[HCl]) a turnover in the reaction mechanism takes place under acidic conditions. At any given MeOH content, the plot of kobs or t1/2 values against acidity is S-shaped, the inflexion point depending upon the MeOH concentration and the temperature. Similar S-shaped variations are found when plotting the dediazoniation product distribution against the acidity. The acid-dependence of the switch between the homolytic and heterolytic mechanisms suggests the homolytic dediazoniation proceeds via transient diazo ethers. The complex kinetic behaviour can be rationalized by assuming two competitive mechanisms: (i) the spontaneous heterolytic dediazoniation of 4BrBD, and (ii) an O-coupling mechanism in which the MeOH molecules capture ArN2 + to yield a highly unstable Z-adduct which undergoes homolytic fragmentation initiating a radical process. Analyses of the effects of temperature on the equilibrium constant for the formation of the diazo ether and on the rate of splitting of the diazo ether allowed, for the first time, estimation of relevant thermodynamic parameters for the formation of diazo ethers under acidic conditions. The 2008 Royal Society of Chemistry.

AUTOMATED DIAZOMETHANE GENERATOR, REACTOR AND SOLID PHASE QUENCHER

-

Page/Page column 17-18, (2022/03/09)

An automated apparatus (Diazo-M-pen and Diazo-M-cube) for production, utilization and quenching of highly toxic diazomethane comprising of integrated pumps, tubular flow reactor, liquid-liquid micro-separator, solid MOF quencher etc.

Green bromination method

-

Paragraph 0032-0034, (2021/06/13)

The invention discloses a green bromination method, and belongs to the field of green organic chemistry. Under the conditions of room temperature, opening and neutrality, reaction raw materials are aromatic hydrocarbon, olefin, alkyne, tryptamine, tryptophane and derivatives thereof with different functional groups, a bromine source is MBrx (M is Fe , Fe , Ce and the like, and x is 2-3), and the unique oxidant is H2O2. Brominated alkanes, alkenes, aromatic hydrocarbons, pyrrolo-indolines and furo-indolines and derivatives thereof can be produced. The bromination reaction is carried out by using easily available and cheap reagents (such as FeBr2, CeB3 and H2O2) in the market and the solvent, and the method has the characteristics of mild reaction conditions, wide substrate application range, simple steps, easiness in operation and no need of separation, is a green, environment-friendly and safe bromination reaction method, and has a good application prospect.

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung

, p. 12632 - 12642 (2021/10/21)

Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 104-92-7