Dimethylformamide → 2-Methoxy-6-(trifluoromethyl)benzoyl chloride

HRID 2425277Notes

Reaction equation

HRID 2425277 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])C=1C(O)=O.CN(C)C=O>ClCCl>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[C:1]=1[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 150175332-Methoxy-6-(trifluoromethyl)benzoic acid

Product 1

HCID 150175342-Methoxy-6-(trifluoromethyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (3 mL, 34.27 mmol) was added dropwise to a mixture of 2-methoxy-6-(trifluoromethyl)benzoic acid (1.5 g, 6.81 mmol) (prepared according to known method, see: EP0897904B1), N,N-dimethylformamide (0.3 mL), and dichloromethane (40 mL) with stirring at rt. The reaction mixture was stirred overnight. Evaporation of solvent and excess oxalyl chloride and drying under vacuum afforded 2-methoxy-6-(trifluoromethyl)benzoyl chloride as a solid, which was used without purification.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customEvaporation of solvent and excess oxalyl chloride
  3. customdrying under vacuum

Sources & evidence

ORD record
ord-4e262c1058c143bba1573018afca2816
Source dataset
uspto-grants-2011_06
Patent number
US07964646B2

Reaction notes

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