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TCI Practical Example: Trifluoromethylthiolation Reaction Using Silver(I) Trifluoromethanethiolate

We are proud to present the trifluoromethylthiolation reaction of 4-methoxybenzyl alcohol using silver(I) trifluoromethanethiolate. Silver(I) trifluoromethanethiolate is known as a trifluoromethylthiolating agent and can directly convert alcoholic hydroxy groups into trifluoromethylthio groups.

Used Chemicals

• Silver(I) Trifluoromethanethiolate [S0977]
• Tetrabutylammonium Iodide (= TBAI) [T0057]
• 4-Methoxybenzyl Alcohol [M0107]
• Toluene

Procedure

Silver(I) trifluoromethanethiolate (907 mg, 4.34 mmol), tetrabutylammonium iodide (4.81 g, 13.0 mmol) and 4-methoxybenzyl alcohol (200 mg, 1.45 mmol) were dissolved in toluene (15 mL) and stirred at 80 °C for 19 hours. The reaction mixture was cooled to room temperature and filtered through a plug of silica gel (eluted with ethyl acetate). The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane) to give (4-methoxybenzyl)(trifluoromethyl)sulfane as a colorless oil (216 mg, 67% yield).

Experimenter's Comments

The reaction mixture was monitored by NMR.

Analytical Data

(4-Methoxybenzyl)(trifluoromethyl)sulfane

¹H NMR (270 MHz, CDCl₃); δ 7.26 (d, 2H, J = 8.4 Hz), 6.86 (d, 2H, J = 8.4 Hz), 4.09 (s, 2H), 3.80 (s, 3H).

Lead Reference

• Direct Dehydroxytrifluoromethylthiolation of Alcohols Using Silver(I) Trifluoromethanethiolate and Tetra-n-butylammonium Iodide
  • J.-B. Liu, X.-H. Xu, Z.-H. Chen, F.-L. Qing, Angew. Chem. Int. Ed. 2015, 54, 897.