Dimethyl Sulfoxide → ((1,1-Dimethylethyl)thio)benzene

Participants

Reaction Steps

In the drybox, 133.7 mg (0.75 mm) of (Me3C)2PH(S), 170.0 mg (0.75 mm) of Pd(OAc)2 and 10.0 mL of DMSO were loaded into a reactor (50 mL) equipped with a magnetic stir bar. The resulting mixture was stirred at room temperature for 12 h. Next, 2.0 g (17.7 mm) of chlorobenzene, 1.35 g (15.0 mm) of t-butylthiol, and 2.16 g (22.5 mm) of NaO—tBu were added into the reactor. The resulting mixture was refluxed for 12 h. The reaction mixture was then cooled to room temperature, chromatographed on silicon gel using t-butylmethylether/hexane (1% volume ratio) as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to yield 812 mg (33% yield) of t-butyl phenyl sulfide. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ7.4-7.2 (m, 5H), 1.17 (s, 9H) ppm. 13C NMR (125 MHz, CDCl3): δ137.4, 132.7, 128.5, 128.3, 45.6, 30.9 ppm. HRMS: Calcd for C10H15S(M++H): 167.0894. Found: 167.0888.

Provenance & Evidence