2-Phenylthiophene → 2-(p-Chlorophenylthio)-5-phenylthiophene

Participants

Reaction Steps

A solution of 40 g (0.250 mole) of 2-phenylthiophene in 200 ml of carbon tetrachloride was treated at room temperature with 45 g (0.252 mole) of p-chlorobenzenesulfenyl chloride. Iron powder (0.1 g) was added and the reaction mixture was allowed to stand for seven days at room temperature. Filtration removed a small amount of insoluble material. Evaporation of the filtrate gave a residue of 79.8 g of crude product, m.p. 85°-87° C. Recrystallization of the residue from 400 ml of absolute ethanol gave 40 g (53%) of 2-(p-chlorophenylthio)-5-phenylthiophene, m.p. 101°-103° C.

Provenance & Evidence