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PHENYLMAGNESIUM BROMIDE solution best Grignard reagents
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Phenylmagnesium bromide
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Amadis Chemical offer CAS#100-58-3;CAT#A800238
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Phenylmagnesium bromide
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PHENYLMAGNESIUM BROMIDE
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Magnesium, bromophenyl-
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CAS NO.100-58-3 Magnesium, bromophenyl-
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100-58-3 Usage

Chemical Properties

Clear light brown to brown solution when properly

Related chemical reaction

1. Phenylmagnesium bromide can react with ferric chloride to give the coupling product. Cyclopentadienyl magnesium bromide can react with ferric chloride to give ferrocene. 2. It can react with chromium trichloride in diethyl ether solution to generate dibenzenechromium. 3. Hexaphenyldilead can be used as the antioxidant of polyphenylene ether lubricant that can be produced from the reaction of lead chloride with phenyl lithium or phenyl magnesium bromide. 4. Take tetrahydrofuran as the solvent, have phenylmagnesium bromide reacted with germanium tetrachloride to obtain tetraphenyl germane. 5. It can be obtained through the low-temperature reaction between lead chloride and phenylmagnesium bromide (Or phenyllithium) in the presence of iodobenzene to derive tetraphenyl lead. 6. Sodium tetraphenylborate is mainly used for the determination of potassium ion, ammonium ion, rubidium ion and cesium ion. It can be obtained with the following process: phenylmagnesium bromide is interacted with boron trifluoride/diethyl ether to generate Tetraphenylboron magnesium bromide first. Evaporate the diethyl ether; add water and then used the calculated amount of sodium carbonate for treatment to obtain it. The above information is edited by the chemicalbook of Dai Xiongfeng.

Reduction agent for preparation of metal carbonyl compound

In 1890, L.Mond found that when carbon monoxide was burned after being put through the active metal nickel powder, it emitted green light flame. After the resulting gas was cooled, he could obtain colorless liquid (melting point 298K, the boiling point of 316K); if this gas is flowed through a heated glass tube, then it can be seen that the metallic nickel was deposited on the wall. This gas is tetracarbonyl nickel Ni(CO)4. Since the 1960s, people have synthesized a hundreds kinds of such carbonyl compounds and their derivatives. Almost all of the transition metal can form such compounds. This kind of special complex formed through transition metal with carbon monoxide ligands is called metal carbonyls, otherwise known as carbonyl complexes. Metal carbonyl occupies an important position in both theoretical research and practical application in modern inorganic chemistry. Preparation of metal carbonyl compound can usually via the following methods: 1. Direct synthesis. Most metal carbonyl complexes are prepared by direct combination between metal and carbon monoxide. However, the metal must be new reduction products, and is in a very activated state. 2. Reduction carbonylation effect at high pressure. Apply reducing agent under high pressure to enable the carbonylation reaction between the metal and carbonyl group with the major reducing agents mainly including hydrogen, active metals, phenylmagnesium bromide (C6H5MgBr) and so on. 3. With thermal decomposition or UV irradiation decomposition, we can obtain certain polynuclear carbonyl compounds. 4. Two different kinds of metal carbonyl compounds can interact with each other to give hetero-nuclear carbonyl compound.
InChI:InChI=1/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5BrMg/c7-8-6-4-2-1-3-5-6/h1-5H

100-58-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (P2025)  Phenylmagnesium Bromide (16% in Tetrahydrofuran, ca. 1mol/L)   100-58-3 250g 300.00CNY Detail
Alfa Aesar (H54729)  Phenylmagnesium bromide, 3M in 2-MeTHF    100-58-3 100ml 917.0CNY Detail
Alfa Aesar (87326)  Phenylmagnesium bromide, 3M in ether    100-58-3 0.25mole 483.0CNY Detail
Alfa Aesar (87326)  Phenylmagnesium bromide, 3M in ether    100-58-3 1mole 1636.0CNY Detail
Alfa Aesar (42859)  Phenylmagnesium bromide, 3M in ether, packaged under Argon in resealable ChemSeal? bottles    100-58-3 0.5mole 763.0CNY Detail
Aldrich (331376)  Phenylmagnesiumbromidesolution  1.0 M in THF 100-58-3 331376-50ML 469.17CNY Detail
Aldrich (331376)  Phenylmagnesiumbromidesolution  1.0 M in THF 100-58-3 331376-100ML 526.50CNY Detail
Aldrich (331376)  Phenylmagnesiumbromidesolution  1.0 M in THF 100-58-3 331376-800ML 1,016.73CNY Detail
Aldrich (703575)  Phenylmagnesiumbromidesolution  2.9 M in 2-methyltetrahydrofuran 100-58-3 703575-100ML 1,385.28CNY Detail
Aldrich (703575)  Phenylmagnesiumbromidesolution  2.9 M in 2-methyltetrahydrofuran 100-58-3 703575-800ML 5,769.27CNY Detail

100-58-3SDS

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 phenylmagnesium bromide

1.2 Other means of identification

Product number -
Other names Phenylmagnesiumbromide,3Minether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:100-58-3 SDS

100-58-3Synthetic route

bromobenzene
108-86-1

bromobenzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 40℃; for 0.25h; Inert atmosphere; Flow reactor;100%
With magnesium In tetrahydrofuran
With magnesium In diethyl ether at 19.9℃; Rate constant; various concentrations of aryl halide;
2-amino-5-chlorobenzonitrile
5922-60-1

2-amino-5-chlorobenzonitrile

A

(2-amino-5-chlorophenyl)-phenyl-methane-imine
5606-39-3

(2-amino-5-chlorophenyl)-phenyl-methane-imine

B

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
A 92%
B n/a
bromobenzene
108-86-1

bromobenzene

A

1-phenyltetrafluoro-2-propenylacetate

1-phenyltetrafluoro-2-propenylacetate

B

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium In tetrahydrofuranA 24%
B n/a
1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

dichlorobis(triphenylphosphine)palladium[II]

dichlorobis(triphenylphosphine)palladium[II]

Diisobutylaluminium hydride(1 M solution in tetrahydrofuran, 4.9 mL, 4.9 mmol)

Diisobutylaluminium hydride(1 M solution in tetrahydrofuran, 4.9 mL, 4.9 mmol)

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
In tetrahydrofuran; toluene
bromobenzene
108-86-1

bromobenzene

N-Z-(S)-serine methyl ester

N-Z-(S)-serine methyl ester

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether
bromobenzene
108-86-1

bromobenzene

(S)-Carbomethoxy oxazolidinone

(S)-Carbomethoxy oxazolidinone

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
In tetrahydrofuran
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With ammonium chloride
[NitriphosCl]PF6

[NitriphosCl]PF6

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With biphenyl; ethylmagnesium bromide; phenylmagnesium bromide In o-xylene
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With hydrogenchloride; iodine In magnesium
bromobenzene
108-86-1

bromobenzene

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium
bromobenzene
108-86-1

bromobenzene

1-methyl-3-fluoro-5,7-dichloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one
60628-69-5

1-methyl-3-fluoro-5,7-dichloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one

A

3-fluorodiazepam

3-fluorodiazepam

B

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With HF In tetrahydrofuran
bromobenzene
108-86-1

bromobenzene

dimethyl-2,3-O-cyclohexylidene-L-tartrate

dimethyl-2,3-O-cyclohexylidene-L-tartrate

A

(-)-2,3-O-cyclohexylidene-1,1,4,4-tetra-phenyl-L-threitol

(-)-2,3-O-cyclohexylidene-1,1,4,4-tetra-phenyl-L-threitol

B

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium In diethyl etherA 17 g (34%)
B n/a
bromobenzene
108-86-1

bromobenzene

magnesium
7439-95-4

magnesium

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
In tetrahydrofuran
In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;
With iodine In tetrahydrofuran for 2h; Inert atmosphere; Reflux;
With iodine In tetrahydrofuran for 1h; Grignard Reaction; Heating / reflux;
bromobenzene
108-86-1

bromobenzene

magnesium

magnesium

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With diethyl ether
bromobenzene
108-86-1

bromobenzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With diethyl ether untersucht wurde die Geschwindigkeit;
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone at -20℃; Product distribution / selectivity;100%
With iron(III) chloride; 1,2-dichloro-ethane In tetrahydrofuran at 0℃; for 0.0833333h; Ionic liquid; Inert atmosphere;100%
With 1,2-bisperfluorotolyl-3,3,4,4,5,5-hexafluorocyclopentene In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere;99%
chlorobenzene
108-90-7

chlorobenzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
nickel(II) In tetrahydrofuran for 18h; Product distribution; other catalyst, other solvents; other Grignard compounds and alkyl or vinyl halides;100%
With CpNi[1-(ethoxycarbonyl)methyl-3-(3,5-dimethylbenzyl)benzimidazolin-2-ylidene]Br In tetrahydrofuran at 25℃; for 3h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;97%
With Pd/Al(OH)3 In toluene at 140℃; for 36h; Kumada Cross-Coupling; Inert atmosphere;94%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

5,6,7,8-tetrachloro-3,4-dihydro-1,4-ethanonaphthalen-2(1H)-one

5,6,7,8-tetrachloro-3,4-dihydro-1,4-ethanonaphthalen-2(1H)-one

5,6,7,8-tetrachloro-1,4-dihydro-9-hydroxy-9-phenyl-1,4-ethanonaphthalene

5,6,7,8-tetrachloro-1,4-dihydro-9-hydroxy-9-phenyl-1,4-ethanonaphthalene

Conditions
ConditionsYield
In diethyl ether for 4h; Ambient temperature;100%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

5,6,7,8-tetrachloro-3,4-dihydro-1,4-ethanonaphthalen-2(1H)-one

5,6,7,8-tetrachloro-3,4-dihydro-1,4-ethanonaphthalen-2(1H)-one

5,6,7,8-tetrachloro-1,4-dihydro-9-endo-hydroxy-9-phenyl-1,4-ethanonaphthalene

5,6,7,8-tetrachloro-1,4-dihydro-9-endo-hydroxy-9-phenyl-1,4-ethanonaphthalene

Conditions
ConditionsYield
In diethyl ether for 4h; Ambient temperature;100%
benzoyl chloride
98-88-4

benzoyl chloride

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

benzophenone
119-61-9

benzophenone

Conditions
ConditionsYield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0℃;100%
Stage #1: benzoyl chloride With 1-methyl-pyrrolidin-2-one In toluene at 0℃; for 0.5h;
Stage #2: phenylmagnesium bromide In tetrahydrofuran; toluene at -10 - 0℃; for 4.25h; chemoselective reaction;
89%
In 2-methyltetrahydrofuran at 25℃; for 1h; Solvent; Concentration; Flow reactor; Green chemistry;85%
3-phenylbutanoyl chloride
51552-98-8

3-phenylbutanoyl chloride

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1,3-diphenylbutane-1-one
1533-20-6

1,3-diphenylbutane-1-one

Conditions
ConditionsYield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0℃;100%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

methyl 1-benzylpyrazole-3-carboxylate
7188-98-9

methyl 1-benzylpyrazole-3-carboxylate

(1-Benzyl-1H-pyrazol-3-yl)-diphenyl-methanol

(1-Benzyl-1H-pyrazol-3-yl)-diphenyl-methanol

Conditions
ConditionsYield
In tetrahydrofuran100%
methyl 3,3-dimethylglutarate
19184-67-9

methyl 3,3-dimethylglutarate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

3,3-dimethy-5,5-diphenyl-5-hydroxypentanoic acid lactone
53392-28-2

3,3-dimethy-5,5-diphenyl-5-hydroxypentanoic acid lactone

Conditions
ConditionsYield
In tetrahydrofuran 2 h; reflux, 2,5 h;100%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate
197460-36-9

methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate

(S)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate
197460-37-0

(S)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate

Conditions
ConditionsYield
In diethyl ether at 0℃; Inert atmosphere; Reflux;100%
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 7h;25%
In diethyl ether at 0℃;
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(4-Methoxy-phenyl)-(4-phenyl-phthalazin-1-yl)-methanone
204520-35-4

(4-Methoxy-phenyl)-(4-phenyl-phthalazin-1-yl)-methanone

(4-Methoxy-phenyl)-phenyl-(4-phenyl-phthalazin-1-yl)-methanol
204520-30-9

(4-Methoxy-phenyl)-phenyl-(4-phenyl-phthalazin-1-yl)-methanol

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Ambient temperature;100%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(2R,9S)-2,9-diphenyl-1-aza-4-oxabicyclo[4.3.0]nonane
205526-47-2

(2R,9S)-2,9-diphenyl-1-aza-4-oxabicyclo[4.3.0]nonane

(2S,6R,1'R)-N-2'-hydroxy-1'-phenylethyl-2,6-diphenylpiperidine
205526-49-4

(2S,6R,1'R)-N-2'-hydroxy-1'-phenylethyl-2,6-diphenylpiperidine

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 72h;100%
para-bromotoluene
106-38-7

para-bromotoluene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)-imidazolium][Ni(PPh3)Cl3] In tetrahydrofuran at 30℃; for 1h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;100%
With C70H40Cl2F68N2O6Pd2 In tetrahydrofuran at 100℃; for 0.0166667h; Kumada coupling reaction; Microwave irradiation;96%
With C17H36ClN6NiP2(1+)*Cl(1-) In tetrahydrofuran for 6h; Reagent/catalyst; Kumada Cross-Coupling; Inert atmosphere;96%
3-(3-bromophenyl)-N-methoxy-N-methylpropanamide
937375-28-5

3-(3-bromophenyl)-N-methoxy-N-methylpropanamide

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

3-(3-bromophenyl)-1-phenyl-propan-1-one
65565-12-0

3-(3-bromophenyl)-1-phenyl-propan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 0℃; for 2h;100%
(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
884510-86-5

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(R)-tert-butyl 3-benzoylpiperidine-1-carboxylate
884510-87-6

(R)-tert-butyl 3-benzoylpiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 1.25h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water for 0.333333h;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water
100%
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 1.25h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.333333h;
100%
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

C13H10BrN

C13H10BrN

Conditions
ConditionsYield
Stage #1: 3-cyanobromobenzene; phenylmagnesium bromide In tetrahydrofuran at 20 - 60℃; for 4h;
Stage #2: With methanol In tetrahydrofuran at 0℃;
100%
Stage #1: 3-cyanobromobenzene; phenylmagnesium bromide In tetrahydrofuran at 20 - 60℃; for 4h;
Stage #2: With methanol In tetrahydrofuran at 0℃;
4-butanolide
96-48-0

4-butanolide

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1,1-diphenylbutan-1,4-diol
1023-94-5

1,1-diphenylbutan-1,4-diol

Conditions
ConditionsYield
With hydrogenchloride; ammonium chloride In tetrahydrofuran100%
Stage #1: 4-butanolide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 10℃; Cooling with ice;
In tetrahydrofuran Grignard reaction; Reflux;
3-Ethoxycyclohex-2-en-1-one
5323-87-5

3-Ethoxycyclohex-2-en-1-one

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

3-phenylcyclohex-2-enone
10345-87-6

3-phenylcyclohex-2-enone

Conditions
ConditionsYield
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran
100%
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran
100%
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃;
100%
2-fluoropyridine
372-48-5

2-fluoropyridine

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-phenylpyridine
1008-89-5

2-phenylpyridine

Conditions
ConditionsYield
Stage #1: 2-fluoropyridine; phenylmagnesium bromide; bis(acetylacetonate)nickel(II); ((2-hydroxymethyl)phenyl)diphenylphosphine In diethyl ether for 0.5h;
Stage #2: With methanol In diethyl ether Product distribution / selectivity;
100%
Stage #1: 2-fluoropyridine; phenylmagnesium bromide; 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether for 2h;
Stage #2: With methanol In diethyl ether Product distribution / selectivity;
96%
2-bromo-3,5-bis(methoxymethoxy)-6-phenylbenzaldehyde
860155-48-2

2-bromo-3,5-bis(methoxymethoxy)-6-phenylbenzaldehyde

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1-[2-bromo-3,5-bis(methoxymethoxy)-6-phenylphenyl]-1-phenylmethanol
860155-59-5

1-[2-bromo-3,5-bis(methoxymethoxy)-6-phenylphenyl]-1-phenylmethanol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃; for 2h;100%
N-(2-Diethylaminoethyl)-4'-(1-oxo-2-phenylbutyl)methanesulfonanilide
58233-95-7

N-(2-Diethylaminoethyl)-4'-(1-oxo-2-phenylbutyl)methanesulfonanilide

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

N-(2-Diethylaminoethyl)-4'-(1-hydroxy-1,2-diphenylbutyl)methanesulfonanilide
58233-96-8

N-(2-Diethylaminoethyl)-4'-(1-hydroxy-1,2-diphenylbutyl)methanesulfonanilide

Conditions
ConditionsYield
With hydrogenchloride; ammonium chloride In diethyl ether; water100%
N-carbethoxytropinone
32499-64-2

N-carbethoxytropinone

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

C16H21NO3
861853-58-9

C16H21NO3

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 5h;100%
(Et2C2B4H4)(Cp)TaCl2
162476-46-2

(Et2C2B4H4)(Cp)TaCl2

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(Et2C2B4H4)(Cp)TaPh2

(Et2C2B4H4)(Cp)TaPh2

Conditions
ConditionsYield
In diethyl ether; toluene Ar-atmosphere; stirring (1 h); filtering, evapn. (vac.), extg. (CH2Cl2), filtering, evapn., washing (pentane);100%
In tetrahydrofuran
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(Z)-3-Trimethylstannanyl-hept-2-enal
180070-95-5, 180070-96-6

(Z)-3-Trimethylstannanyl-hept-2-enal

1-phenyl-3-trimethylstannyl-hept-2-ene-1-al
180071-40-3, 180071-39-0

1-phenyl-3-trimethylstannyl-hept-2-ene-1-al

Conditions
ConditionsYield
In diethyl ether Ar-atmosphere; slight excess PhMgBr, refluxing for 12 h; addn. of satd. aq. NH4Cl, extn. of aq. layer (Et2O), drying (MgSO4), solvent removal; isomer mixt. not sepd., detd. by (119)Sn-NMR spectroscopy;100%
1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde
917494-83-8

1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol
1025762-60-0

(1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol

Conditions
ConditionsYield
Stage #1: 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
100%
Stage #1: 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
100%
5-formyl-N,N-dimethyl-1H-indole-1-carboxamide
1025763-25-0

5-formyl-N,N-dimethyl-1H-indole-1-carboxamide

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

5-(hydroxy(phenyl)methyl)-N,N-dimethyl-1H-indole-1-carboxamide
1025763-27-2

5-(hydroxy(phenyl)methyl)-N,N-dimethyl-1H-indole-1-carboxamide

Conditions
ConditionsYield
Stage #1: 5-formyl-N,N-dimethyl-1H-indole-1-carboxamide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; for 2h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether
100%
In tetrahydrofuran100%
trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester
126613-08-9

trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1-bromo-2-phenylnaphthalene
22082-93-5

1-bromo-2-phenylnaphthalene

Conditions
ConditionsYield
Stage #1: trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester With 1,3-bis-(diphenylphosphino)propane; lithium bromide; tris-(dibenzylideneacetone)dipalladium(0) In diethyl ether at 20℃; for 0.0833333h;
Stage #2: phenylmagnesium bromide In diethyl ether at 0 - 20℃; for 7h;
100%
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); lithium bromide In diethyl ether at 0℃; for 18h; Inert atmosphere;
With bis(diphenylphosphino)propanepalladium(II) dichloride; lithium bromide In diethyl ether for 1h; Inert atmosphere; Cooling with ice;17 g
(3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one
645396-79-8

(3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(2S,3E,4aR,10aR)-3-benzylidene-4a-ethyl-2-phenyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-2,7-diol
645396-80-1

(2S,3E,4aR,10aR)-3-benzylidene-4a-ethyl-2-phenyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-2,7-diol

Conditions
ConditionsYield
Stage #1: phenylmagnesium bromide With cerium(III) chloride In tetrahydrofuran at -78℃; for 1.5h;
Stage #2: (3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one In tetrahydrofuran at -40℃; for 2h;
Stage #3: With water; acetic acid In tetrahydrofuran
100%
Stage #1: phenylmagnesium bromide With cerium(III) chloride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;
Stage #2: (3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one In tetrahydrofuran at -70 - -40℃; for 2.5h; Inert atmosphere;
96%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide
537030-19-6

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-1-hydroxy-5-phenylpyrrolidine
1000612-60-1

(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-1-hydroxy-5-phenylpyrrolidine

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 3h;100%
3,6-di(piperidin-1-yl)-9H-xanthen-9-one
1023903-94-7

3,6-di(piperidin-1-yl)-9H-xanthen-9-one

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

C29H31N2O(1+)*Cl(1-)
1174713-22-4, 1079889-38-5

C29H31N2O(1+)*Cl(1-)

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃;100%
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