Oxalyl chloride → 2,4,5-Trifluorobenzoyl chloride

HRID 1650145Notes

Reaction equation

HRID 1650145 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O>CCOCC.CN(C)C=O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 5211702,4,5-Trifluorobenzoic acid

Product 1

HCID 1451642,4,5-Trifluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.24 g of 2,4,5-trifluorobenzoic acid in 50 ml of ether containing two drops of N,N-dimethylformamide was added, under argon, oxalyl chloride dropwise over 30 minutes. Stirring was continued for an additional 30 minutes when gas evolution ceased. The ether was removed in vacuo and the residue vacuum distilled to give 5.07 g of the desired compound, bp 26°-27° C./0.75 mm.

Workup

  1. customThe ether was removed in vacuo
  2. distillationthe residue vacuum distilled

Sources & evidence

ORD record
ord-d7a30655ba1d441ba12f6cb2071fa816
Source dataset
uspto-grants-1990_05
Patent number
US04923868

Reaction notes

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