Bromine → Methyl 5-bromo-3-methyl-2-furoate

Participants

Reaction Steps

To a solution of methyl 3-methylfuran-2-carboxylate (3.0 g, 21.41 mmol) in ethyl ether (100 mL) was added bromine (1.210 mL, 23.55 mmol) dropwise at RT and the mixture was allowed to stir for 14 h. Evaporation followed by purification by flash chromatography (silica gel, 0% to 10% ethyl acetate in hexanes) yielded the title compound (4.0 g, 85% yield) as a white solid: 1H NMR (500 MHz, CDCl3) δ 6.31 (s, 1H), 3.88 (s, 3H), 2.33 (s, 3H); HPLC retention time: 2.776 min, LCMS (ES): m/z 219, 221 [M+H]+.

Provenance & Evidence