p-Chlorothiophenol → 4-Chlorobenzenesulfenylchloride

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chlorothiophenol, 1 (20.15 g, 0.139 mol) in 170 mL of anhydrous carbon tetrachloride was placed in a 0.5 L 3-neck round bottom flask equipped with a magnetic stirrer, thermocouple, addition funnel, nitrogen line, heating mantle, condenser and caustic scrubber to absorb acidic gases (SO2 and HCl). A catalytic amount of pyridine (3 mL) was added to the solution, and the flask's content was chilled to ˜10° C. Sulfuryl chloride (55.2 g, 0.409 mol) was slowly added to the solution of 1, and the reaction mixture was gently refluxed for 3 hours. The resulting red solution was cooled to room temperature, quickly filtered through glass wool, and concentrated by rotary evaporation to yield 23 g of 4-chlorobenzene sulfenyl chloride, 2 as a viscous red oil. This crude material was used immediately for preparation of 4.

Provenance & Evidence