Sodium hydride → 2,2,2-Trifluoro-1-(4-fluorophenyl)ethyl trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

NaH (11.87 g, 296.7 mmol) was added to Et2O (700 mL) at 0° C. under N2 and a solution of 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol (44.3 g, 228.2 mmol) in ether was added at 0° C. under N2. The reaction mixture was stirred 10 min at 0° C. then 1 h at room temperature. Trifluoromethanesulfonyl chloride (50 g, 296.7 mmol) in Et2O was added at 0° C. under N2 and the reaction mixture was stirred 10 min at 0° C. and then 3 h at room temperature. The solvent was removed under the reduced pressure and H2O (100 mL) was added slowly. The aqueous layer was extracted by hexane and the combined organic layer was dried with MgSO4. The solvent was removed under the reduced pressure to give trifluoromethanesulfonic acid 2,2,2-trifluoro-1-(4-fluorophenyl)ethyl ester (70 g, 90% d.e) as colorless oil.

Provenance & Evidence