Acetic Anhydride → HCID 13920896, compound

Participants

Reaction Steps

A stirred solution of 2-bromothiophenol (100 g, 0.529 mol), acetic anhydride (62.4 mL, 0.661 mol), and 4-dimethylaminopyridine (3.2 g, 0.026 mol) in dichloromethane (1000 mL) was cooled in an ice-bath. Triethylamine (92.2 mL, 0.662 mol) was slowly added, and then the ice bath was removed. The mixture was stirred at room temperature for 1 hour. Water (10 mL) was added, and after a couple of minutes the mixture was washed with aqueous 1N hydrochloric acid (3×300 mL), 10% sodium hydroxide solution (3×300 mL), and 1N hydrochloric acid (300 mL), and then dried (Na2SO4), and filtered. Evaporation of the solvent left S-2-bromophenyl ethanethioate as a pale yellow oil (104 g).

Provenance & Evidence