1-Methylimidazole → 1-(3-Chloro-4-fluorophenyl)propan-2-one

Participants

Reaction Steps

To a solution of 2-(3-chloro-4-fluorophenyl)acetic acid (18.46 g, 97.89 mmol) in acetic anhydride (463 mL) was added N-methylimidazole (3.9 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution and organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a colorless oil (14.5 g, 79%). 1H NMR (400 MHz, CDCl3) δ 7.23 (dd, J=6.9, 2.1 Hz, 1H), 7.14-7.00 (m, 2H), 3.66 (s, 2H), 2.19 (s, 3H).

Provenance & Evidence