Bromine → HCID 71185532, compound

Participants

Reaction Steps

Liquid bromine (1.8 g, 0.57 ml, 11.43 mmol) was added drop wise to a stirred solution of methyl-5-(4-methoxyphenyl)-4-methylthiophene-2-carboxylate (prepared according to the procedure reported in WO 2007/092751, 2.0 g, 7.62 mmol) in acetic acid (20 ml) at a temperature of about 25° C. The resulting mixture was stirred at the same temperature for 16 hours. The progress of reaction was monitored by TLC. The reaction mixture was poured onto ice water (100 ml). The mixture so obtained was extracted with ethyl acetate (3×100 ml). The separated combined organic layer was washed with 10% aqueous sodium bicarbonate solution (2×50 ml). The organic layer was then dried over anhydrous Na2SO4. The solvent was evaporated form the organic layer under reduced pressure to obtain a crude product. The crude product was further purified by flash chromatography using 15-25% ethyl acetate in hexanes as an eluent to obtain the title compound (2.35 g, 90%).

Provenance & Evidence