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

HRID 889871

Reaction equation

HRID 889871 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 Chloride2×HCID 27569594-Bromo-2,2-diphenylbutyric acid

Product 1

HCID 222500664-Bromo-2,2-diphenylbutyric chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Bromo-2,2-diphenylbutyric acid (Compound B(1), 23 g, 72 mmol) was suspended in 150 mL of chloroform, and 20 mL of thionyl chloride (270 mmol) was added dropwise. After addition of the thionyl chloride, 0.2 mL of dimethylformamide was added and the resulting solution heated at reflux for about 4 h. The reaction mixture was then concentrated under reduced pressure to provide 4-bromo-2,2-diphenylbutyric chloride (Compound D(1)) as a pale yellow oil that was used in the following step without further purification.

Workup

  1. additionwas added
  2. temperaturethe resulting solution heated
  3. temperatureat reflux for about 4 h
  4. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-b0821871a2314e6695b0528c5606f54e
Source dataset
uspto-grants-2006_02
Patent number
US06995168B2

Linked notes

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