2,2,2-Trifluoroethyl Triflate for 2,2,2-Trifluoroethyl Etherification

2,2,2-Trifluoroethyl Triflate for 2,2,2-Trifluoroethyl Etherification

2,2,2-Trifluoroethyl Triflate (CF3CH2OTf, TCI code T1604) is a reagent for introducing the 2,2,2-trifluoroethyl group through etherification. In the TCI practical example, it is used for the 2,2,2-trifluoroethyl etherification of 4'-hydroxyacetophenone. The hydroxyl group is first deprotonated with sodium hydride (60% dispersion in paraffin liquid) in DMF at room temperature for 10 minutes. 2,2,2-Trifluoroethyl Triflate is then added, and the mixture is stirred overnight at 60 °C. After washing with water and brine and purification by silica gel column chromatography, 4'-(2,2,2-trifluoroethoxy)acetophenone is obtained as a pale yellow solid in 71% yield. The reaction is monitored by UPLC, and the product is characterized by 1H NMR (270 MHz, CDCl3).

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