Methyl4-bromofuran-2-carboxylate

54113-41-6

58235-80-6

General procedure for the synthesis of methyl 4-bromofuran-2-carboxylate from methyl 4,5-dibromofuran-2-carboxylate: isopropylmagnesium chloride (2M solution of THF, 38 mL) was added slowly and dropwise to a solution of methyl 4,5-dibromofuran-2-carboxylate (14.2 g, 50 mmol) in anhydrous THF (100 mL) at -40 °C and under nitrogen protection. The reaction mixture was stirred continuously at the same temperature for 1 h. The reaction was subsequently quenched by the addition of water (50 mL). The precipitate was collected by filtration and the filtrate was extracted by partitioning with ethyl acetate and water. The organic phase was washed twice with saturated saline, dried over anhydrous sodium sulfate and purified by silica gel column chromatography to afford the target product, methyl 4-bromofuran-2-carboxylate (11a), as a yellow solid (9 g, 89% yield).1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.51 (s, 1H), 3.82 (s, 3H).