Sulfuric Acid → 2-Chloro-5-[(trifluoroacetamido)methyl]benzoic acid

Participants

Reaction Steps

To a solution of 2-chlorobenzoic acid (500 mg, 3.49 mmol) in cone. H2SO4 was added 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (547 mg, 3.49 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was poured into ice-water and the precipitate obtained, was collected by filtration, dried and the re-crystallized from toluene/butan-2-one (7:1) to afford 800 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 13.47 (br s, 1H), 10.06 (br s, 1H), 7.71 (s, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.43 (d, J=9.9 Hz, 1H), 4.42 (d, J=6.0 Hz, 2H); MS (m/z): 280.18 (M−H)−.

Provenance & Evidence