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

HRID 448809

Reaction equation

HRID 448809 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=O)C>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 (D) (Aldrich Chemical Company, Inc.) (23 g, 72 mmol) was suspended in chloroform (150 mL), and thionyl chloride (20 mL) was added dropwise. After addition of thionyl chloride, DMF (0.2 mL) was added, and the resulting solution was heated at reflux for 4 hours. The reaction mixture was then concentrated under reduced pressure to provide 4-bromo-2,2-diphenylbutyric acid chloride (E) as a pale yellow oil that was used for next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-220ebb96453644fca7e51a9f5a6e1e52
Source dataset
uspto-grants-2013_07
Patent number
US08481743B2

Linked notes

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