Water → Methyl 4-bromo-5-methylfuran-2-carboxylate

Participants

Reaction Steps

To a solution of methyl 5-methyl-2-furancarboxylate (2.33 g, 16.29 mmol) and aluminum chloride (3.3 g, 24.75 mmol) in chloroform (50 ml) at room temperature was added Br2 (1.1 ml, 21.35 mmol). The resulting solution was stirred at room temperature in a 150 mL sealed tube reactor for 2 hours. Upon completion, the solution was cooled in an ice bath, H2O added and reaction partitioned between CHCl3/H2O. The organic layer was washed with NaHCO3 and then Na2S2O3. The organic layer was dried with Na2SO4, concentrated, adsorbed onto silica and purified via column chromatography (0-20% EtOAc/Hexanes) affording the title compound (2.13 g, 9.72 mmol, 60%): LC-MS (ES) m/z=221 (M+H)+.

Provenance & Evidence