Trifluoroiodomethane (ca. 10％ in Tetrahydrofuran, ca. 0.5mol/L)

• 4-Bromobenzenethiol [B1385]
• Trifluoroiodomethane (ca. 10% in Tetrahydrofuran, ca. 0.5mol/L) [T3957]
• Sodium Hydride (60%, dispersion in Paraffin Liquid) [S0481]
• Dry THF

To a solution of 4-bromothiophenol (200 mg, 1.05 mmol) in THF (2 mL) was added NaH (51 mg, 1.27 mmol, 1.2 eq.) slowly at r.t. for 10 min. Then, trifluoroiodomethane (ca. 10% in tetrahydrofuran, ca. 0.5mol/L) (3 mL, 1.59 mmol, 1.5 eq.) was added to the reaction mixture and stirred at the same temperature for overnight. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with water (15 mL) and brine (15 mL), then organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane on silica gel), giving 4-bromophenyl trifluoromethyl sulfide as a colorless liquid (177 mg, 65%).

The reaction mixture was monitored by UPLC.

4-Bromophenyl Trifluoromethyl Sulfide

¹H NMR (270 MHz, CDCl₃); δ 7.57 (d, 2H, J = 8.9 Hz), 7.52 (d, 2H, J = 8.4 Hz).

• Convenient synthesis and isolation of trifluoromethylthio-substituted building blocks
• A. Harsányi, É. Dorkó, Á. Csapó, T. Bakó, C. Peltz, J. Rábai, J. Fluor. Chem. 2011, 132, 1241.