Thionyl Chloride → 3-Nitro-5-(trifluoromethyl)benzoyl chloride

HRID 452990Notes

Reaction equation

HRID 452990 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].S(Cl)([Cl:19])=O>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([Cl:19])=[O:8])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 226083993-Nitro-5-(trifluoromethyl)benzoyl chloride

Procedure

A solution of 3-nitro-5-(trifluoromethyl)benzoic acid (2.00 g, 8.51 mmol) in thionyl chloride (12.4 ml, 170 mmol) was heated at 90° C. for 2 hours. The solution was cooled to room temperature, concentrated, and azeotroped with toluene to provide 3-nitro-5-(trifluoromethyl)benzoyl chloride as a liquid.

Workup

  1. concentrationconcentrated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-b4a247cdd43344568779fb562d08b5ea
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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