Thionyl Chloride → 2-Bromo-5-(trifluoromethyl)benzoyl chloride

HRID 2064494Notes

Reaction equation

HRID 2064494 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:17])=O>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([Cl:17])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 152610132-Bromo-5-(trifluoromethyl)benzoic acid

Product 1

HCID 790215092-Bromo-5-(trifluoromethyl)benzoyl chloride

Procedure

A solution of 2-bromo-5-(trifluoromethyl)benzoic acid (10 g, 37.2 mmol) in thionyl chloride (44.2 g, 372 mmol) was heated at 90° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and then azeotroped with toluene to afford 2-bromo-5-(trifluoromethyl)benzoyl chloride, which was used directly in the next step.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-5784c005443042faaa25e2d914992027
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

Loading…