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

HRID 279073

Reaction equation

HRID 279073 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 chlorideYield 94.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Bromo-2,2-diphenylbutyric acid 23 g (72 mmol) was suspended in 150 mL of chloroform. At room temperature, 20 mL (270 mmol) of thionyl chloride was added dropwise to the resulting suspension. After addition of 0.2 mL of dimethylformamide, the resulting mixture was heated under reflux for 4 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, whereby 23 g (yield: 94.7%) of 4-bromo-2,2-diphenylbutyric chloride was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customAfter completion of the reaction
  4. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-18aefa498618404db98a73d8d2df4637
Source dataset
uspto-grants-2002_03
Patent number
US06362203B1

Linked notes

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