p-Chlorothiophenol → 4-Chlorobenzenesulfenylchloride

Temperature

10 °C

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.

1. customequipped with a magnetic stirrer
2. additionthermocouple, addition funnel
3. temperaturenitrogen line, heating mantle, condenser and caustic scrubber
4. customto absorb acidic gases (SO2 and HCl)
5. additionA catalytic amount of pyridine (3 mL) was added to the solution
6. temperaturethe reaction mixture was gently refluxed for 3 hours
7. temperatureThe resulting red solution was cooled to room temperature
8. filtrationquickly filtered through glass wool
9. concentrationconcentrated by rotary evaporation

ORD record

ord-3242044b9d834604b00536aa58cef6f0

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710210B2