Hydrogen Peroxide → 2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[CH2:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].B1C2CCCC1CCC2.[OH-].[Na+].OO.[O-:34]S([O-])=O.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][OH:34])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:17]([F:18])([F:19])[F:20]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-chloro-2-(trifluoromethyl)-4-(4-vinylphenoxy)benzene (3 g, 10.04 mmol) in THF (50 mL) was added 9-BBN (24.11 mL, 12.05 mmol) under nitrogen. The reaction mixture was stirred at 0° C. for 0.5 h, then the temperature was allowed to warm up to room temperature. NaOH (13.39 mL, 40.2 mmol) and H2O2 (14.36 mL, 141 mmol) was added. The mixture was then heated at 60° C. for 2 h. Na2SO3 was added to quench the reaction after cooling. Purification via flash chromatography then afforded the title compound (2.2 g, 6.95 mmol, 69.2% yield). LCMS: rt=3.55 min, [M+H+-H2O]=299
Workup
- temperatureto warm up to room temperature
- temperatureThe mixture was then heated at 60° C. for 2 h
- customto quench
- customthe reaction
- temperatureafter cooling
- customPurification via flash chromatography
Sources & evidence
- ORD record
- ord-323e6639f90244a0bb7cbb9da3c14e07
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637536B2
Reaction notes
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