Trifluoromethylthiolating Agent for Direct Dehydroxytrifluoromethylthiolation of Alcohols
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Silver(I) Trifluoromethanethiolate [S0977] is known as a trifluoromethylthiolating agent and can directly convert alcoholic hydroxy groups into trifluoromethylthio groups. As an example, 4-Methoxybenzyl Alcohol [M0107] was reacted with Silver(I) Trifluoromethanethiolate [S0977] and Tetrabutylammonium Iodide (= TBAI) [T0057] in toluene at 80 °C for 19 hours. After filtration through a silica gel plug and purification by silica gel column chromatography, (4-Methoxybenzyl)(trifluoromethyl)sulfane was obtained as a colorless oil in 67% yield. The reaction was monitored by NMR. The procedure is reported in the lead reference on direct dehydroxytrifluoromethylthiolation of alcohols using Silver(I) Trifluoromethanethiolate and tetra-n-butylammonium iodide, published in Angew. Chem. Int. Ed. 2015, 54, 897. The 1H NMR data (270 MHz, CDCl3) showed 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).
Related products
- TCI S0977 811-68-7 Silver(I) Trifluoromethanethiolate
- TCI T0057 311-28-4 Tetrabutylammonium Iodide
- TCI M0107 105-13-5 4-Methoxybenzyl Alcohol
Source
- TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20251006
- TCI product page S0977: tcichemicals.com/ID/en/p/S0977
For research and laboratory use only, not for human consumption.
