Acetic Acid → HCID 86666826, compound

Participants

Reaction Steps

To a solution of 1-(5-fluoro-2-hydroxy-4-methylphenyl)ethanone (2.2 g, 13 mmol) and acetic acid (20 mL, 400 mmol) was added N-bromosuccinimide (2.8 g, 16 mmol). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo, neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. Purification on silica gel with ethyl acetate/hexanes (0-50%) gave 1-(3-Bromo-5-fluoro-2-hydroxy-4-methylphenyl)ethanone (2.3 g, 71%). 1H NMR (400 MHz, CDCl3): δ 12.80 (s, 1H), 7.40 (m, 1H), 2.60 (s, 3H), 2.40 (s, 3H).

Provenance & Evidence