Hydrochloric Acid → 1-(2,4-Difluorophenyl)-2,2,2-trifluoroethan-1-ol
Reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[F:11][C:12]([F:14])([F:13])[CH:4]([C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1])[OH:5]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
2,4-Difluorobenzaldehyde (1.1 mL, 10.0 mmol) and (trifluoromethyl)trimethylsilane (1.77 mL, 12.0 mmol) were dissolved in THF (25 mL) and then cooled to 0° C. To this, 1M TBAF in THF (76 μL, 76 μmol) was added and the reaction mixture was allowed to warm to room temperature. After 3.25 h, 2.5M HCl (25 mL) was added. The reaction was stirred for 1 h and then extracted with ether. The organic layer was washed with brine and dried with Na2SO4. The solvent was removed under the reduced pressure to give 2,2,2-trifluoro-1-(2,4-difluoro-phenyl)ethanol (2.5 g) as a racemic mixture.
Workup
- temperatureto warm to room temperature
- extractionextracted with ether
- washThe organic layer was washed with brine
- dry with materialdried with Na2SO4
- customThe solvent was removed under the reduced pressure
Sources & evidence
- ORD record
- ord-85b58a424fc4426299e11fe5d2c7df16
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893093B2
Reaction notes
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