Thionyl Chloride → 1-(Chloromethyl)-4-(phenylthio)benzene

Participants

Reaction Steps

The 1-hydroxymethyl-4-phenylthiobenzene (3.0 g) is dissolved in methylene chloride (15 ml), and thereto is added with stirring thionyl chloride (1.5 ml) under ice cooling. The mixture is stirred for one hour, and the reaction mixture is washed with ice water (10 ml×3), and thereto is added methylene chloride (50 ml). The mixture is washed in order with 5% aqueous sodium hydrogen carbonate solution (5 ml×3) and saturated aqueous sodium chloride solution (30 ml×2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 1-chloromethyl-4-phenylthiobenzene (3.0 g).

Provenance & Evidence