Dimethylformamide → 4-Bromo-2,2-diphenylbutyric chloride

HRID 279077

Reaction equation

HRID 279077 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](O)=[O:6].S(Cl)([Cl:22])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Br:1][CH2:2][CH2:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([Cl:22])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27569594-Bromo-2,2-diphenylbutyric acid

Product 1

HCID 222500664-Bromo-2,2-diphenylbutyric chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 5 mL of chloroform was suspended 5.00 g (15.7 mmol) of 4-bromo-2,2-diphenylbutyric acid. Thionyl chloride (10 mL) was then added dropwise at room temperature. To the resulting mixture was added 0.1 mL of dimethylformamide, followed by heating under reflux for 5 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, whereby 4-bromo-2,2-diphenylbutyric chloride was obtained. While stirring under ice cooling, 50 mL of cold methanol was added. The temperature was allowed to rise back to room temperature, and then stirring was conducted for 30 minutes. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 5.00 g (yield: 95.7%) of methyl 4-bromo-2,2-diphenylbutyrate was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction
  4. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-249d93f2ca6e439a9e0194fd75c26ef6
Source dataset
uspto-grants-2002_03
Patent number
US06362203B1

Linked notes

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