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

HRID 1367815Notes

Reaction equation

[H-].[Na+].[F:3][C:4]([F:15])([F:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[OH:6].[F:16][C:17]([F:23])([F:22])[S:18](Cl)(=[O:20])=[O:19]>CCOCC>[F:15][C:4]([F:3])([F:14])[CH:5]([O:6][S:18]([C:17]([F:23])([F:22])[F:16])(=[O:20])=[O:19])[C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

custom1 h
customat room temperature
stirringthe reaction mixture was stirred 10 min at 0° C.
custom3 h
customat room temperature
customThe solvent was removed under the reduced pressure and H2O (100 mL)
additionwas added slowly
extractionThe aqueous layer was extracted by hexane
dry with materialthe combined organic layer was dried with MgSO4
customThe solvent was removed under the reduced pressure

Sources & evidence

ORD record: ord-2d70f4cfd2434672a0ff3c785b70289d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893093B2

Reaction notes

Loading…