p-Chlorothiophenol → 2-Fluoro-6-(4-chlorophenylthio)benzonitrile

Participants

Reaction Steps

4-Chlorobenzenethiol (1.14 g; 7.9 mmol) in anhydrous DMF is added over 1 hour to an ice-cooled suspension of sodium hydride, 60% dispersion in mineral oil (316 mg; 7.9 mmol), in anhydrous DMF. The reaction is allowed to room temperature over 30 minutes. This material is then added over 30 minutes to an ice-cooled solution of 2,6-difluorobenzonitrile (1.0 g; 7.2 mmol) in anhydrous DMF. After the addition the reaction is allowed to room temperature and stirred for 2 hours. The reaction mixture is then poured slowly into vigorously stirred ice water to give a white paste, which becomes solid with continued stirring. The solid is filtered, washed with water, and dried under vacuum at 30° C. overnight to yield 1.66 grams of 2-(4-chlorophenylsulfanyl)-6-fluorobenzonitrile.

Provenance & Evidence