Chlorosuccinimide → Chloromethyl p-Tolyl Sulfide

Participants

Reaction Steps

Methyl p-tolyl sulfide (75 g, 542.27 mmol) was diluted in chorobenzene (452 mL). N-Chloro Succinimide (NCS) (76.07 g, 1.05 eq) was added in small portions maintaining the temperature between 35° C. and 45° C., under an argon atmosphere. The reaction mixture was stirred at the same temperature range until the reaction was complete. After that time, the solution turned into a suspension. The suspension formed was filtered and the solid was washed with chlorobenzene (50 ml). The filtrate was washed with water (3×225 mL). The resulting organic phase was dried with magnesium sulfate and concentrated. The crude product was purified by distillation to give 102.68 g (100%) of the desired product as yellow oil (bp: 96° C. at 40 Pa).

Provenance & Evidence