Oxalyl chloride → 2-Methyl-3,4,6-trifluorobenzoyl chloride

HRID 1081402

Reaction equation

HRID 1081402 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[C:7]([CH3:13])[C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:17])=O>CN(C=O)C.ClCCl>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[C:7]([CH3:13])[C:3]=1[C:4]([Cl:17])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 101303052-Methyl-3,4,6-trifluorobenzoic acid

Product 1

HCID 150076072-Methyl-3,4,6-trifluorobenzoyl chlorideYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.8 g (30.5 mmol) of 2,4,5-trifluoro- 6-methylbenzoic acid, 4.7 g (37.0 mmol) of oxalyl chloride, and 100 mL of dichloromethane was treated with three drops of DMF. The reaction mixture was stirred at room temperature for 2 hours, then concentrated to give 6.3 g of the title compound as an oily solid. The product was used "as is" in the next step.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-03d9906dc62b4e37b49606ae98496391
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Linked notes

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