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

HRID 2246425Notes

Reaction equation

HRID 2246425 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 acid2×

Product 1

HCID 222500664-Bromo-2,2-diphenylbutyric chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Bromo-2,2-diphenylbutyric acid (compound (F), 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 hours. The reaction mixture was then concentrated under reduced pressure to provide 4-bromo-2,2-diphenylbutyric acid chloride (compound (G) 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 hours
  4. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-994d538318024065a5e0f62c20d48348
Source dataset
uspto-grants-2010_03
Patent number
US07687518B2

Reaction notes

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