1,2-Dimethoxyethane → 1-(4-Chlorophenylsulfonylmethyl)-3-methoxybenzene

Participants

Reaction Conditions

Reaction Steps

A dimethoxyethane (10 ml) suspension of sodium 4-chlorobenzenesulfinate (210 mg, 1.06 mmol) and 3-methoxybenzyl chloride (154 μl, 1.06 mmol) was stirred at 70° C. for 16 hours. After cooling to room temperature, butanol (2 ml) and tetrabutylammonium bromide (45 mg) were added and the resulting mixture was stirred further at 70° C. for 16 hours. After cooling the reaction mixture to room temperature, the solvent was concentrated under reduced pressure. Ethyl acetate was added to the residue. The mixture was washed successively with water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate (=5:1) eluate was concentrated under reduced pressure, whereby the title compound (216 mg, 69%) was obtained as a white solid.

Provenance & Evidence