Cornforth reagent → 1-(5-Bromo-2-fluorophenyl)ethanone

Participants

Reaction Steps

To a solution of 1-(5-bromo-2-fluoro-phenyl)-ethanol (37 g, 168 mmol) in CH2Cl2 (400 mL) and pyridinium dichromate (127 g, 337 mmol) were added molecular sieves (10 g). The mixture was stirred at room temperature for 20 hours. The mixture was filtered through diatomaceous earth, washed with CH2Cl2 (3×100 mL) and concentrated. The crude product was purified by column chromatography (60-120 mesh silica gel) using 10% ethyl acetate in pet-ether to afford of 1-(5-bromo-2-fluoro-phenyl)-ethanone (23 g, 63%) as pale brown oil. 1H NMR (CDCl3): δ 7.9-8.1 (d, 1H), 7.5-7.7 (m, 1H), 6.95-7.1 (t, 1H), 2.6-2.7 (d, 3H).

Provenance & Evidence