Thionyl Chloride → 2,6-Dichloro-4-trifluoromethylbenzoyl chloride

HRID 1598509Notes

Reaction equation

HRID 1598509 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([Cl:15])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:18])=O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([Cl:15])[C:3]=1[C:4]([Cl:18])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 116804602,6-dichloro-4-(trifluoromethyl)benzoic Acid

Product 1

HCID 189294232,6-Dichloro-4-trifluoromethylbenzoyl chlorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 20.4 g of 2,6-dichloro-4-trifluoromethylbenzoic acid (11), 18.8 g of thionyl chloride and a small amount of anhydrous N,N-dimethylformamide was stirred at 90° C. overnight. The thionyl chloride was distilled off, and the resulting residue was distilled under reduced pressure to obtain 21.7 g of the desired compound in the form of a colorless liquid (quantitative yield).

Workup

  1. distillationThe thionyl chloride was distilled off
  2. distillationthe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-7a32fdb285fa48ccaa7cbeffaa86ce13
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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