Oxalyl chloride → 2,3,4,5-Tetrafluorobenzoyl chloride

HRID 2290517Notes

Reaction equation

HRID 2290517 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C)C=O>[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([Cl:17])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2975492,3,4,5-Tetrafluorobenzoic acid

Product 1

HCID 27336892,3,4,5-Tetrafluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 30.0 g (155 mmol) of 2,3,4,5-tetrafluorobenzoic acid in 75 ml of dichloromethane was added 14.8 ml (1.1 equivalents) of oxalyl chloride. The mixture was then treated with three drops of dry N,N-dimethylformamide and the vigorous reaction was stirred at room temperature overnight. The mixture was then concentrated to an oil, was taken up in toluene, and reconcentrated to afford 2,3,4,5-tetrafluorobenzoyl chloride which was used in the next step.

Workup

  1. customthe vigorous reaction
  2. concentrationThe mixture was then concentrated to an oil

Sources & evidence

ORD record
ord-7a85952e72e247c3b5e11afc07f5aa42
Source dataset
uspto-grants-1986_10
Patent number
US04617308

Reaction notes

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