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

A dried 50 mL of flask was charged sodium hydride, 60% dispersion in mineral oil (624 mg, 15.6 mmol) under N2 and then washed with dried hexane (20 mL) twice. Dried ethyl ether (10 mL) was added and a solution of 2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethanol (90% ee) (2.5 g, 12.89 mmol) in ethyl ether (10 mL) was added at 0° C. After completion of addition, the reaction mixture was allowed to warm up to room temperature and stirred for 1 h. A solution of trifluoromethanesulfonyl chloride (3.28 g, 19.5 mmol) in ethyl ether (10 mL) was added at 0° C. After completion of addition, the reaction was allowed to warm up to room temperature and stirred for 1 h. The solvent was removed under rot-vap and diluted with hexane (150 mL) and washed with a saturated NaHCO3 n and brine. After drying with MgSO4, the organic solvent was removed to give trifluoro-methanesulfonic acid 2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethyl ester (3.15 g) (90% ee) as a colorless oil which was used in the next step without further purification.

1. washwashed with dried hexane (20 mL) twice
2. additionDried ethyl ether (10 mL) was added
3. additionAfter completion of addition
4. additionAfter completion of addition
5. temperatureto warm up to room temperature
6. stirringstirred for 1 h
7. customThe solvent was removed under rot-vap
8. additiondiluted with hexane (150 mL)
9. washwashed with a saturated NaHCO3 n and brine
10. dry with materialAfter drying with MgSO4
11. customthe organic solvent was removed

ORD record

ord-3cc666148f194a53958c7168c695c258

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547701B2