CHLOROMETHYL PHENYL SULFOXIDE

Chloromethyl phenyl sulfoxide has been used in the preparation of:

• 1-chloroalkyl sulfoxides
• starting material for the synthesis alkyl sulfoxides and thiol ester acyl anion equivalent

Chlorination of methylphenyl sulfoxide with sulfonyl chloride in dichloromethane or N-chlorosuccinimide in chloroform gives Chloromethyl phenyl sulfoxide in good yields. A one-step process starting from phenyl sulfide involves chlorination with sulfonyl chloride in dichloromethane followed by oxidation with the same reagent in the presence of wet silica gel. Another method uses silver(I) nitrate and sulfonyl chloride in acetonitrile.

Journal of the American Chemical Society, 90, p. 4496, 1968 DOI: 10.1021/ja01018a078
Synthesis, p. 831, 1986
Tetrahedron Letters, 17, p. 613, 1976

Chloromethyl phenyl sulfoxide has synthetic potential and exhibits unusual stereochemical specificity. Stereospecific hydroxyalkylation of chloromethyl phenyl sulfoxide has been investigated.