Chlorine → p-t-Butylbenzenesulfenyl chloride

Participants

Reaction Steps

To a mixture of 332 grams (2.0 moles) of 4-(tert-butyl)thiophenol and 800 ml of carbon tetrachloride was slowly added with stirring and cooling a solution of 150 grams (2.0+ moles) of chlorine in 600 ml of carbon tetrachloride at 0° C. After chlorine addition was complete the mixture was stirred at 0°-10° C. for two hours, hydrogen chloride and carbon tetrachloride removed in vacuo and the residue was distilled in a one-foot packed column to give 378 grams of 4-(tert-butyl)phenylsulfenyl chloride, b.p. 95°-97°/1.0 mm (yield 94%).

Provenance & Evidence