Water → 1-(5-Bromofuran-2-yl)ethan-1-one

Participants

Reaction Steps

To a solution of 2-acetylfuran (20 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (22 mmol) with stirring. The reaction mixture was stirred overnight, then poured onto cold water. The product was extracted with ether (200 mL, 3× times). Yield 61%, mp 92-93° C. (hexanes/ether, Lit. mp 94-95° C.; see Gilman H., et al., J. Am. Chem. Soc., 53, 4192-4196 (1931). 1H NMR (CDCl3); δ 2.45 (s, 3H), 6.49 (d, J=3.9 Hz, 1H), 7.12 (d, J=3.6 Hz, 1H). 13C NMR; δ 8185.4, 154.4, 128.2, 118.9,114.3, 25.7.

Provenance & Evidence