Benzyl Bromide → 2,3-Dichloro-1-methoxy-4-[(phenylmethyl)thio]benzene

Participants

Reaction Steps

A solution of 6.23 g of 2,3-dichloro-4-methoxythiophenol in 60 ml of sieve-dried dimethylformamide is added to 0.75 g of sodium hydride over a period of 2-3 minutes. After stirring at room temperature for 20 minutes, the yellowish solution is treated with 5.10 g of benzyl bromide at a rate so that the temperature does not rise above 40°. Stirring is continued for an additional 30 minutes. The cloudy mixture is poured onto 200 g of crushed ice with caution and the white precipitate is collected on a filter after 1 hour at 10° C. The air-dried product is recrystallized from acetone-hexane to give 7.8 g of 4-benzylthio-2,3-dichloroanisole as white needles, mp 116°-117° C.

Provenance & Evidence