N-bromobutanimide → N-benzyl-5-bromo-3-methylfuran-2-carboxamide

Participants

Reaction Steps

To a stirred solution of N-benzyl-3-methylfuran-2-carboxamide (1.18 g, 5.49 mmol) in acetonitrile (25 mL) was added N-bromosuccinimide (0.98 g, 5.49 mmol). The reaction mixture was stirred for 16 hours, and then partitioned between ethyl acetate (100 mL) and water (75 mL). The organic layer was washed with 1 N sodium hydroxide solution (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 0-20% ethyl acetate in hexanes to afford N-benzyl-5-bromo-3-methylfuran-2-carboxamide as a colorless solid (0.18 g, 11%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.27 (m, 5H), 6.54 (br s, 1H), 6.28 (s, 1H), 4.58 (d, J=5.9 Hz, 2H), 2.40 (s, 3H); MS (ES+) m/z 294.1 (M+1), 296.1 (M+1).

Provenance & Evidence