Oxalyl chloride → 3-Chloro-2,4,5-trifluorobenzoyl chloride

HRID 622581Notes

Reaction equation

HRID 622581 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5](O)=[O:6].C(Cl)(=O)C([Cl:17])=O>CN(C)C=O.ClCCl>[Cl:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([Cl:17])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27342693-Chloro-2,4,5-trifluorobenzoic Acid

Product 1

HCID 27822453-Chloro-2,4,5-trifluorobenzoyl chlorideYield 28.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 9.4g (45 mmol) of 3-chloro-2,4,5-trifluorobenzoic acid, oxalyl chloride (7.6 g, 60 mmol), 3 drops of dimethylformamide, and 100 ml of dichloro-methane was stirred at room temperature for three hours. The solvent and excess oxalyl chloride were evaporated on the steam bath, and the residue was distilled at 121°-123° C. at 30 mm Hg to give 2.9 g of the title compound.

Workup

  1. customThe solvent and excess oxalyl chloride were evaporated on the steam bath
  2. distillationthe residue was distilled at 121°-123° C. at 30 mm Hg

Sources & evidence

ORD record
ord-ecc32570b7344cd187b1775e6b1f6af5
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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