Acetic Acid → 1-(3-Bromo-5-chloro-4-fluoro-2-hydroxyphenyl)ethanone

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Reaction Steps

To a stirred solution of 1-(5-chloro-4-fluoro-2-hydroxyphenyl)ethanone (7.9 g, 42 mmol) in acetic acid (80 mL, 1.0 mol) was added N-bromosuccinimide (9.0 g, 50 mmol) and the resulting mixture was stirred at rt for 18 h. The reaction mixture was 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, and concentrated to dryness under reduced pressure. The residue was purified on silica gel, eluting with 0 to 20% ethyl acetate in hexane, to yield the desired product (93% yield). 1H NMR (300 MHz, CDCl3): δ 13.15 (s, 1H), 7.79 (m, 1H), 2.62 (s, 3H).

Provenance & Evidence