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

HRID 2219107Notes

Reaction equation

HRID 2219107 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-8f8226da58f242b28cfaa45e9efb877f
Source dataset
uspto-grants-2008_08
Patent number
US07414062B2

Reaction notes

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