Triethylamine → 4-fluoro-N-methyl-2-(trifluoromethyl)benzamide

Participants

Reaction Steps

DMF (3 drops) and oxalyl chloride (2.55 ml) were added to a mixture of 4-fluoro-2-(trifluoromethyl)benzoic acid (5.50 g) and dichloromethane (50 ml), followed by stirring at room temperature for 3 hours. The reaction solution was added dropwise to a 2M methylamine-THF solution (17.3 ml) and a solution of triethylamine (5.55 ml) in dichloromethane (50 ml) under ice cooling, followed by stirring for 30 minutes and concentration under reduced pressure, addition of water and extraction with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution and then saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with diisopropylether to obtain 4-fluoro-N-methyl-2-(trifluoromethyl)benzamide (4.37 g) as a white solid.

Provenance & Evidence