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

HRID 17005

Reaction equation

HRID 17005 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]>CCCCCC.C(OCC)C>[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

6

Reactant 3

HCID 24758Sodium hydrideHCID 79000Trifluoromethanesulfonyl chlorideHCID 111482462,2,2-Trifluoro-1-(4-fluorophenyl)ethanol

Product 1

HCID 575620972,2,2-Trifluoro-1-(4-fluorophenyl)ethyl trifluoromethanesulfonateYield 101.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

NaH (640 mg, 16 mmol, 60% in mineral oil) was washed twice with hexane (20 mL) and then suspended in dried diethyl ether (20 mL). A solution of 2,2,2-trifluoro-1-(4-fluoro-phenyl)ethanol (1.94 g, 10 mmol) in diethyl ether (10 mL) was added at 0° C. After stirring for 2 h at room temperature, a solution of trifluoromethanesulfonyl chloride (1.68 g, 10 mmol) in diethyl ether (10 mL) was added. After 2 h, the reaction mixture was quenched by adding a solution of NaHCO3 and the product was extracted with diethyl ether. The extracts were washed with brine and dried, and the solvent was removed to yield trifluoromethanesulfonic acid 2,2,2-trifluoro-1-(4-fluorophenyl)ethyl ester (3.3 g).

Workup

  1. waitAfter 2 h
  2. customthe reaction mixture was quenched
  3. additionby adding a solution of NaHCO3
  4. extractionthe product was extracted with diethyl ether
  5. washThe extracts were washed with brine
  6. customdried
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-28c59b0678af4521a6e78ceace972cf5
Source dataset
uspto-grants-2010_06
Patent number
US07737300B2

Linked notes

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