Acetic Acid → Methyl 2-phenylsulfonylethyl sulfide

Participants

Reaction Conditions

Reaction Steps

To a three-neck 50 mL round bottom flask equipped with a temperature probe, magnetic stirring, and bleach scrubber was charged in sequence 3.43 g (20.39 mmol) phenyl vinyl sulfone followed by 5 mL of acetonitrile, and the mixture was then cooled in an ice-water bath. To this mixture was then added 2.53 g (42.13 mmol) of glacial acetic acid in one portion. To this mixture was con-added 10 g (21.40 mmol) of a 15 wt % sodium thiomethoxide in water solution over a 17 min period. The internal reaction temperature rose from 14° C. to 17° C. during the sodium thiomethoxide addition. The ice-water bath was removed and the reaction mixture was heated to 50-60° C. for 3.5 h at which time liquid chromatography (LC) analysis indicated about 42% (relative area) of starting phenyl vinyl sulfone in the reaction mixture. Another 4.76 g (10.19 mmol) of a 15 wt % sodium thiomethoxide in water solution was added over a 9 min period. The reaction mixture was then stirred an additional 6.5 h at 50-60° C., and then cooled to ambient temperature and allowed to stir overnight. At this time LC analysis indicated about 7% (relative area) of starting phenyl vinyl sulfone in the reaction mixture. To the reaction mixture was added 1.37 g (23.44 mmol) of sodium chloride and the reaction phases were allowed to separate. The organic layer was concentrated on a rotary evaporator to give 3.96 g of methyl 2-phenylsulfonylethyl sulfide as a yellow oil (yield was ˜90% based on theoretical yield). 1H NMR (300 MHz, CDCl3) δ 2.1 (s, 3H), 2.78 (m, 2H), 3.35 (m 2H), 7.1 (m, 2H), 7.7 (m, 1H), 7.9 (m, 2H). 13C NMR (75.5 MHz, CDCl3) δ 15.5, 26.4, 56.0, 127.9, 129.4, 134.1, 138.6.

Provenance & Evidence