Sodium hydride → trifluoro-methanesulfonic acid (R)-2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propyl ester

Temperature

0 °C

A 60% suspension of NaH in oil (2.35 g, 58.8 mmol) was washed several times with hexanes and after suspending it in anhydrous ethyl ether (100 mL), (R)-2,2,3,3,3-pentafluoro-1-(4-fluoro-phenyl)propan-1-ol (12.0 g, 49 mmol) in ether (20 mL) was added slowly at room temperature. After stirring for 15 min, the reaction mixture was cooled at 0° C. and trifluoromethylsulfonyl chloride (12.38 g, 73.7 mmol) was added. The reaction mixture was stirred for 1:30 h at 0° C., then concentrated under reduced pressure and the residue was diluted with hexane (100 mL). The reaction mixture was washed with sat. sol. NaHCO3, brine and dried over magnesium sulfate. After removing the solvent on rotovapor, trifluoro-methanesulfonic acid (R)-2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propyl ester was obtained as a colorless oil (16.0 g).

1. stirringThe reaction mixture was stirred for 1
2. concentration30 h at 0° C., then concentrated under reduced pressure
3. additionthe residue was diluted with hexane (100 mL)
4. washThe reaction mixture was washed with sat. sol. NaHCO3, brine
5. dry with materialdried over magnesium sulfate
6. customAfter removing the solvent on rotovapor

ORD record

ord-0996aabc028f4af5b2ed5d5e2893a086

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893093B2