4-[2,2,2-Trifluoro-1-[(trimethylsilyl)oxy]ethyl]morpholine

Trifluoromethylation of Aryl Iodides²⁾: A Schlenk tube is charged with CuI (0.030 mmol, 5.7 mg), 1,10-phenanthroline (0.030 mmol, 5.4 mg) and CsF (0.60 mmol, 67.3 mg). The tube is evacuated and backfilled with argon, and then diglyme (0.60 mL), 4-nitroiodobenzene (0.30 mmol, 74.7 mg), and 1 (0.60 mmol, 154 mg) are added. The resulting reaction mixture is stirred at 80 °C for 24 h. After the reaction is complete, the mixture is cooled to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic layers are washed with brine, dried over MgSO₄, filtered, and the volatiles are removed in vacuo. The residue is purified by chromatography on silica gel to yield 4-nitrobenzotrifluoride (77% yield).