4399-47-7

Basic information

• Product Name: Cyclobutyl bromide
• Synonyms: BROMOCYCLOBUTANE;CYCLOBUTYL BROMIDE;Cyclobutane, bromo-;Cyclobutane,bromo-;Cyclobutylbromide,96%;Bromocyclobutane,95%;Cyclobutyl bromide, pure, 97%;Cyclobutyl halide
• CAS NO: 4399-47-7
• Molecular Formula: C₄H₇Br
• Molecular Weight: 135
• EINECS: 224-530-9
• Product Categories: Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;Cycloalkanes;Pyridines ,Halogenated Heterocycles
• Mol File: 4399-47-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 108 °C(lit.)
• Flash Point: 72 °F
• Appearance: Clear colorless/Liquid
• Density: 1.434 g/mL at 25 °C(lit.)
• Vapor Pressure: 32mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble
• Sensitive: Light Sensitive
• BRN: 1900415
• CAS DataBase Reference: Cyclobutyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutyl bromide(4399-47-7)
• EPA Substance Registry System: Cyclobutyl bromide(4399-47-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 10-36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-16
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 8
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 4399-47-7(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

InChI:InChI=1/C4H7Br/c5-4-2-1-3-4/h4H,1-3H2

Synthetic route

1-bromo-4-butene (5162-44-7) + 4-methoxy-3-pyridinesulfonamide (1229666-20-9) → 1,4-dihydro-1-methyl-4-oxo-3-pyridinesulfonamide + Bromocyclobutane (4399-47-7)

Conditions	Yield
In acetonitrile at 20℃; for 84h; Reflux; regioselective reaction;	A 75% B 37.5%

Cyclopropylmethanol (2516-33-8) → Bromocyclobutane (4399-47-7) + cyclopropylcarbinyl bromide (7051-34-5)

Conditions	Yield
With hydrogen bromide In 1,4-dioxane; chloroform at 10 - 20℃; for 2h;	A 9% B 74%
With phosphorus tribromide In diethyl ether at -80℃; Product distribution; variation of temperatures;
With hydrogen bromide; 1-octyl-3-methyl-imidazolium bromide at 25℃; for 0.333333h; Reagent/catalyst; Temperature;

Cyclobutancarbonsaeure - Silbersalz (42392-28-9) → Bromocyclobutane (4399-47-7)

Conditions	Yield
With bromine In tetrachloromethane at -25℃; for 12h;	60%
With bromine In tetrachloromethane at 26.9℃; for 1h;	23%

cyclopropylcarbinyl bromide (7051-34-5) → 1-bromo-4-butene (5162-44-7) + Bromocyclobutane (4399-47-7)

Conditions	Yield
With NbCl3(N,N′-bis-(2,6-diisopropylphenyl)-1,4-diaza-2,3-dimethyl-1,3-butadiene) In benzene-d6 at 120℃; for 14h; Catalytic behavior; Inert atmosphere; Schlenk technique; Glovebox;	A 59% B 33%

dimethylacetylene (503-17-3) + 1,1-dibromocyclobutane (33742-81-3) → Bromocyclobutane (4399-47-7) + 1-Brom-1-methylcyclobutan (80204-24-6) + 1,2-dimethylspiro(2.3)hex-1-ene (108909-90-6) + methylene cyclopropane (6142-73-0)

Conditions	Yield
With methyllithium In diethyl ether at -35℃; Further byproducts given;	A n/a B 12% C 21% D 30%

1,1-dibromocyclobutane (33742-81-3) → Bromocyclobutane (4399-47-7) + 1-Brom-1-methylcyclobutan (80204-24-6) + 1,2-dimethylspiro(2.3)hex-1-ene (108909-90-6) + methylene cyclopropane (6142-73-0)

Conditions	Yield
With dimethylacetylene; methyllithium In diethyl ether at -35℃; Further byproducts given;	A n/a B 12% C 21% D 30%

cyclobutanol (2919-23-5) → Bromocyclobutane (4399-47-7)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In diethyl ether

diethyl cyclobutane-1,1-dicarboxylate (3779-29-1) → Bromocyclobutane (4399-47-7)

Conditions	Yield
Multistep reaction;

norborn-2-ene (498-66-8) → Bromocyclobutane (4399-47-7) + 7-anti-Chlor-8,9,10-trinorbornan-2-exo-ol (38537-30-3, 38537-32-5, 38537-61-0, 38537-64-3, 98431-04-0)

Conditions	Yield
With hypochloric acid

Cyclobutanecarboxylic acid (3721-95-7) → Bromocyclobutane (4399-47-7)

Conditions	Yield
With hydroxide; bromine; silver nitrate 2.) CCl4; Multistep reaction;
With [bis(acetoxy)iodo]benzene; potassium bromide In dichloromethane at 25℃; Irradiation;	86 %Chromat.

1,1‐dichlorocyclobutane (1506-77-0) → Bromocyclobutane (4399-47-7) + 1-bromocyclobut-1-ene (33954-15-3) + cyclobutene (822-35-5) + methylene cyclopropane (6142-73-0)

Conditions	Yield
With n-butyllithium at 20℃; under 0.001 Torr; for 0.5h; Yield given. Yields of byproduct given;

bicyclo[1.1.0]butane (157-33-5) → 1-bromo-4-butene (5162-44-7) + Bromocyclobutane (4399-47-7) + cyclopropylcarbinyl bromide (7051-34-5)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; mercury dibromide 1.) CH2Cl2; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen bromide Product distribution; influence of reaction time;

Cyclobutancarbonsaeure - Silbersalz (42392-28-9) → Bromocyclobutane (4399-47-7) + cyclopropylcarbinyl bromide (7051-34-5)

Conditions	Yield
With bromine In tetrachloromethane at -20℃; for 1h; Yield given. Yields of byproduct given;

1-Bromo-1-iodocyclobutane → Bromocyclobutane (4399-47-7) + 1-bromocyclobut-1-ene (33954-15-3) + cyclobutene (822-35-5) + methylene cyclopropane (6142-73-0)

Conditions	Yield
With methyllithium at 20℃; under 0.001 Torr; for 0.5h; Yield given. Yields of byproduct given;

mercury (II)-salt of/the/ cyclobutane-carboxylic acid → Bromocyclobutane (4399-47-7)

Conditions	Yield
With carbon disulfide; bromine at -25℃;

silver salt of/the/ cyclobutane-carboxylic acid → Bromocyclobutane (4399-47-7)

Conditions	Yield
With tetrachloromethane; bromine at -25℃;

silver-salt of/the/ cyclobutanecarboxylic acid → Bromocyclobutane (4399-47-7)

Conditions	Yield
With tetrachloromethane; bromine at -20℃;

Cyclopropylmethanol (2516-33-8) + hydrogen bromide (10035-10-6, 12258-64-9) → 1-bromo-4-butene (5162-44-7) + Bromocyclobutane (4399-47-7) + cyclopropylcarbinyl bromide (7051-34-5)

dichloromethane (75-09-2) + Cyclopropylmethanol (2516-33-8) + phosphorus tribromide (7789-60-8) → 1-bromo-4-butene (5162-44-7) + Bromocyclobutane (4399-47-7) + cyclopropylcarbinyl bromide (7051-34-5)

chloro(cyclopropyl)methane (5911-08-0) → 1-bromo-4-butene (5162-44-7) + Bromocyclobutane (4399-47-7) + cyclopropylcarbinyl bromide (7051-34-5)

Conditions	Yield
With sodium bromide; NaY zeolite In pentane at 25℃; Kinetics;	A 58 % Chromat. B 32 % Chromat. C 10 % Chromat.

Cyclopropylmethanol (2516-33-8) → 1-bromo-4-butene (5162-44-7) + Bromocyclobutane (4399-47-7) + cyclopropylcarbinyl bromide (7051-34-5)

Conditions	Yield
With hydrogen bromide; 3-ethyl-1-methyl-1H-imidazol-3-ium bromide at 80℃; for 0.333333h; Reagent/catalyst; Temperature;

5-methyloxazol-2-yl(phenyl)methanone (526214-00-6) + Bromocyclobutane (4399-47-7) → cyclobutyl-(5-methyl-oxazol-2-yl)-phenyl-methanol (1046818-32-9)

Conditions	Yield
Stage #1: Bromocyclobutane With magnesium; iodine In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: 5-methyloxazol-2-yl(phenyl)methanone In tetrahydrofuran at 20℃; Cooling with ice;	100%
Stage #1: Bromocyclobutane With magnesium In diethyl ether at 20℃; for 1h; Heating / reflux; Stage #2: 5-methyloxazol-2-yl(phenyl)methanone In tetrahydrofuran; diethyl ether at -10 - 20℃; for 16h; Stage #3: With water; ammonium chloride In tetrahydrofuran; diethyl ether at -20℃;	38%

2-(2-hydroxy-3-isopropyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (1092448-19-5) + Bromocyclobutane (4399-47-7) → 2-(2-cyclobutyloxy-3-isopropyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (1092448-20-8)

Conditions	Yield
With caesium carbonate; potassium iodide In N,N-dimethyl-formamide at 130℃; for 2h; Microwave irradiation;	98%

6-chloro-2-hydroxypyridine (16879-02-0) + Bromocyclobutane (4399-47-7) → 2-chloro-6-(cyclobutoxy)pyridine

Conditions	Yield
With potassium carbonate at 80℃; for 16h;	98%

6-chloro-2-pyridone (16879-02-0) + Bromocyclobutane (4399-47-7) → 2-chloro-6-(cyclobutoxy)pyridine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;	98%

Bromocyclobutane (4399-47-7) + methyl 8-hydroxyquinoline-5-carboxylate (260796-38-1) → C15H15NO3

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 95℃; for 16h;	97%

4-bromo-3-fluorobenzenethiol (942473-86-1) + Bromocyclobutane (4399-47-7) → (4-bromo-3-fluorophenyl)(cyclobutyl)sulfane (1614246-39-7)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 70℃; for 19h;	95%

Bromocyclobutane (4399-47-7) + methyl (S)-6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate → (S)-methyl 6-bromo-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions	Yield
With caesium carbonate In acetonitrile at 80℃; for 6h;	95%

Bromocyclobutane (4399-47-7) + 4-((tert-butyldimethylsilyl)oxy)-2-fluorobenzonitrile (175968-15-7) → cyclobutyl(2-fluoro-4-hydroxyphenyl)methanone (1221235-53-5)

Conditions	Yield
Stage #1: Bromocyclobutane With iodine; magnesium; ethylene dibromide In diethyl ether at 20℃; Stage #2: 4-((tert-butyldimethylsilyl)oxy)-2-fluorobenzonitrile With copper(I) bromide In tetrahydrofuran; diethyl ether at 20 - 60℃; for 0.75h; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0 - 60℃; for 1h; Inert atmosphere;	95%

2,3-dimethyl-2,3-butane diol (76-09-5) + Bromocyclobutane (4399-47-7) + benzo[1,3,2]dioxaborole (274-07-7) → 2-cyclobutyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions	Yield
Stage #1: benzo[1,3,2]dioxaborole With bis(cyclopentadienyl)titanium dichloride; potassium carbonate In tert-butyl methyl ether for 0.5h; Stage #2: Bromocyclobutane In tert-butyl methyl ether at 80℃; under 760.051 Torr; for 24h; Inert atmosphere; Stage #3: 2,3-dimethyl-2,3-butane diol With triethylamine In tert-butyl methyl ether at 20℃; for 1h; Inert atmosphere;	95%
Stage #1: benzo[1,3,2]dioxaborole With bis(cyclopentadienyl)titanium dichloride; potassium carbonate In tert-butyl methyl ether for 0.5h; Inert atmosphere; Glovebox; Stage #2: Bromocyclobutane In tert-butyl methyl ether at 80℃; for 24h; Sealed tube; Stage #3: 2,3-dimethyl-2,3-butane diol With triethylamine In tert-butyl methyl ether at 20℃; for 1h; Sealed tube;	95%

5-formyl-2-hydroxy-3-methyl-benzoic acid methyl ester (1092448-55-9) + Bromocyclobutane (4399-47-7) → 2-cyclobutyloxy-5-formyl-3-methyl-benzoic acid methyl ester (1092448-56-0)

Conditions	Yield
With caesium carbonate; potassium iodide In N,N-dimethyl-formamide at 110℃; for 6h;	94%

methyl 2-hydroxy-4-nitrocinnamate + Bromocyclobutane (4399-47-7) → C14H15NO5

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 48h; Inert atmosphere;	94%

2,3-dibromopyridine (13534-89-9) + Bromocyclobutane (4399-47-7) → 3-bromo-2-cyclobutylpyridine

Conditions	Yield
Stage #1: Bromocyclobutane With magnesium In tetrahydrofuran at 60℃; for 3h; Stage #2: With zinc(II) chloride In tetrahydrofuran at -78 - 20℃; for 1h; Stage #3: 2,3-dibromopyridine With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60℃; for 1h; Inert atmosphere;	94%

Bromocyclobutane (4399-47-7) + sodium thiophenolate (930-69-8) → cyclobutyl phenyl sulfide (67132-84-7)

Conditions	Yield
In N,N-dimethyl-formamide for 1.5h; Heating;	93%
In N,N-dimethyl-formamide at 25℃; for 2h;	63%
In N,N-dimethyl-formamide at 0℃; Kinetics;

Bromocyclobutane (4399-47-7) + 3,5-dibromotriazole (7411-23-6) → 3,5-dibromo-1-cyclobutyl-1H-1,2,4-triazole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; Sealed tube; Inert atmosphere;	93%

Bromocyclobutane (4399-47-7) + 6-mercaptopyridine-2-carboxylic acid ethyl ester (1603018-85-4) → 6-cyclobutylsulfanylpyridine-2-carboxylic acid ethyl ester (1609289-69-1)

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 18h;	92%

Bromocyclobutane (4399-47-7) + 3-bromo-4-fluorobenzenethiol (942473-85-0) → (3-bromo-4-fluorophenyl)(cyclobutyl)sulfane

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 60℃; Inert atmosphere;	92%

3-Bromophenol (591-20-8) + Bromocyclobutane (4399-47-7) → 1-bromo-3-(cyclobutoxy)benzene (1268713-64-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;	91%
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 71h; Inert atmosphere;	70%

Bromocyclobutane (4399-47-7) + C8H11LiSi*LiCl → cyclobutyldimethyl(phenyl)silane

Conditions	Yield
Stage #1: C8H11LiSi*LiCl With magnesium bromide In tetrahydrofuran at 66℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: Bromocyclobutane With ferric(III) bromide; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 0℃; for 1.5h; Schlenk technique; Inert atmosphere;	91%

Bromocyclobutane (4399-47-7) + 5-bromo-2-hydroxybenzonitrile (40530-18-5) → 5-bromo-2-cyclobutoxybenzonitrile (1594671-86-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 6h; Inert atmosphere;	90%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Sealed tube;	77%

Bromocyclobutane (4399-47-7) + phenyl isothiocyanate (103-72-0) → N-phenylcyclobutanecarbothioamide

Conditions	Yield
Stage #1: Bromocyclobutane With tert.-butyl lithium at -78℃; for 2h; Inert atmosphere; Stage #2: phenyl isothiocyanate at -78 - 20℃; Inert atmosphere;	90%

ethyl 1H-imidazole-2-carboxylate (33543-78-1) + Bromocyclobutane (4399-47-7) → 1-cyclobutyl-1H-imidazole-2-carboxylic acid ethyl ester

Conditions	Yield
Stage #1: ethyl 1H-imidazole-2-carboxylate With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: Bromocyclobutane In N,N-dimethyl-formamide at 100℃; for 5h;	89.7%
Stage #1: ethyl 1H-imidazole-2-carboxylate With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: Bromocyclobutane In N,N-dimethyl-formamide at 100℃; for 5h;

Bromocyclobutane (4399-47-7) + N-(2-fluorophenyl)pyrimidin-2-amine (138851-61-3) → N-(2-cyclobutyl-6-fluorophenyl)pyrimidin-2-amine

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); lithium tert-butoxide In 1,4-dioxane at 100℃; for 16h; Schlenk technique; Inert atmosphere;	89%
With N,N'-di-tert-butylethylenediamine; C40H32N12Ni2; lithium tert-butoxide In 1,4-dioxane at 120℃; for 16h;	57%

7-Azaindole (271-63-6) + Bromocyclobutane (4399-47-7) → C11H12N2

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 20h;	89%

3-methyl-4-nitrophenol (2581-34-2) + Bromocyclobutane (4399-47-7) → 4-cyclobutoxy-2-methyl-1-nitrobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 14h; Inert atmosphere;	89%

Bromocyclobutane (4399-47-7) + phenylacetylene (536-74-3) → C12H13N3

Conditions	Yield
With sodium azide; sodium L-ascorbate In water at 50℃; for 1h; Green chemistry;	88%

Bromocyclobutane (4399-47-7) + benzyl 3-(4-chloro-3-(((4-methoxybenzyl)oxy)methyl)phenyl)-2,2-dimethylhept-6-ynoate → benzyl 3-(4-chloro-3-(((4-methoxybenzyl)oxy)methyl)phenyl)-5-(1-cyclobutyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoate

Conditions	Yield
Stage #1: Bromocyclobutane With sodium azide In N,N-dimethyl-formamide at 80℃; for 2h; Microwave irradiation; Stage #2: benzyl 3-(4-chloro-3-(((4-methoxybenzyl)oxy)methyl)phenyl)-2,2-dimethylhept-6-ynoate With copper(l) iodide; N-ethyl-N,N-diisopropylamine In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol at 70℃; for 1h; Microwave irradiation;	88%

carbon dioxide (124-38-9) + Bromocyclobutane (4399-47-7) + 2-(1-phenylvinyl)aniline (64097-92-3) → 4-cyclobutylmethyl-4-phenyl-1H-benzo[d][1,3]oxazin-2(4H)-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;	88%

Bromocyclobutane (4399-47-7) + bis(pinacol)diborane (73183-34-3) → 2-cyclobutyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions	Yield
With lithium tert-butoxide In N,N-dimethyl-formamide at 30℃; under 760.051 Torr; for 3h; Irradiation;	87%
With copper(I) oxide; lithium methanolate; pyrographite In ethanol at 20℃; for 12h; Inert atmosphere;	50%
With potassium methanolate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; copper dichloride In tetrahydrofuran at 20℃;

6-methoxypyridine-3-ol + Bromocyclobutane (4399-47-7) → 5-cyclobutoxy-2-methoxypyridine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 16h;	87%

Bromocyclobutane (4399-47-7) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-cyclobutoxybenzonitrile (1065640-60-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 72h;	86%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 72h;

Upstream product

• 498-66-8 norborn-2-ene 
• 503-17-3 dimethylacetylene 
• 33742-81-3 1,1-dibromocyclobutane 
• 2516-33-8 Cyclopropylmethanol 
• 10035-10-6 hydrogen bromide 
• 75-09-2 dichloromethane 
• 7789-60-8 phosphorus tribromide 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 5162-44-7 1-bromo-4-butene 
• 1229666-20-9 4-methoxy-3-pyridinesulfonamide 
• 5911-08-0 chloro(cyclopropyl)methane 
• 42392-28-9 Cyclobutancarbonsaeure - Silbersalz 
• 157-33-5 bicyclo[1.1.0]butane 
• 1506-77-0 1,1‐dichlorocyclobutane 

Downstream Products

• 822-35-5 cyclobutene 
• 190367-36-3 methyl 4-cyclobutyl-2-methylbenzoate 
• 42392-32-5 cyclobutanecarboxylic acid but-3-enyl ester 
• 42392-30-3 cyclobutanecarboxylic acid cyclobutyl ester 
• 42392-31-4 Cyclobutancarbonsaeure-cyclopropylmethylester 
• 871657-76-0 1-(cyclobutylthio)-4-fluorobenzene 
• 625446-15-3 4-bromo-1-cyclobutoxy-2-fluoro-benzene 
• 146374-41-6 2-Aminophenyl cyclobutyl methanone 
• 911227-85-5 C₃₃H₄₂N₂O₅ 
• 126259-92-5 t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-cyclobutylhydroxymethyl]-2,2-dimethyl-3-oxazolidinecarboxylate 
• 287193-18-4 6-cyclobutyl-4-phenoxyquinazoline 
• 635715-44-5 7-(2-Chlorophenyl)-2-cyclobutyloxy-8-(piperazin-1-yl)-1,7-dihydropurin-6-one 
• 13384-48-0 cyclobutylmagnesium bromide 
• 1065640-60-9 3-bromo-4-cyclobutoxybenzonitrile 

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