Acetic Acid → HCID 58669189, compound

Participants

Reaction Steps

To a solution of 2-formyl-3-methyl-4-cyclohexylthiophene (4.1 g, 20 mmol, See Example 22) in 30 mL of a mixture prepared from acetic acid and chloroform (1:1), was added solid N-bromosuccinimide (5.3 g, 30 mmol) slowly in portions at 0° C. The reaction mixture was then stirred overnight at room temperature, poured into water, and extracted repeatedly with dichloromethane. The combined organic layers were washed with saturated NaHCO3 and brine solutions, and dried over anhydrous Na2SO4. After the solvent was removed by rotary evaporation, the remaining solid was purified by column chromatography using silica gel and a dichloromethane-petroleum ether (2:3) as eluant. The solvent was removed by rotary evaporation yielding 3.3 g white solid (57%). 1H NMR (CDCl3) δ 9.97 (s, 1, CHO), 2.88 (m, 1,cyclohexyl methane), 2.59 (s, 3,CH3), 1.87 and 1.34 m, 10, cyclohexyl)

Provenance & Evidence