BENZENESULFINYL CHLORIDE

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 3973, 1992 DOI: 10.1016/0040-4039(92)88076-H

Safety Profile

May explode if stored in a sealedcontainer. When heated to decomposition it emits toxicfumes of SOx and Cl^-.

Synthesis

A mixture of 30.4 g (0.2 mol) of phenyl thioacetate and 20.4 g (0.2 mol) of acetic anhydride is chlorinated at -10 to 0℃. The color changes to yellow, then red, and then back to yellow. The reaction mixture is heated to 80℃ under reduced pressure (3.5 kPa), until the residue begins to boil, after which it is cooled; yield: 31.5–31.8 g (98.1– 99.1%).