Hydrogen Peroxide → 2-(4-(3-(Trifluoromethyl)phenoxy)phenyl)ethanol

HRID 705828Notes

Reaction equation

HRID 705828 reaction equation
B1C2CCCC1CCC2.[F:10][C:11]([F:28])([F:27])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH2:26])=[CH:21][CH:20]=2)[CH:13]=1.[OH-:29].[Na+].OO>C1COCC1>[F:10][C:11]([F:27])([F:28])[C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][OH:29])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677746121-(Trifluoromethyl)-3-(4-vinylphenoxy)benzene

Product 1

HCID 677742022-(4-(3-(Trifluoromethyl)phenoxy)phenyl)ethanolYield 63.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9-BBN (277 mL, 139 mmol) was added to a solution of 1-(trifluoromethyl)-3-(4-vinylphenoxyl)benzene (24.4 g, 92 mmol) in THF (200 mL) at 0° C., and the resulting reaction mixture was stirred at room temperature overnight. To the mixture was added 3M NaOH solution (140 mL) and 30% hydrogen peroxide (123 mL) slowly at 0° C., and the reaction mixture was stirred at 50° C. for 2 h. Purification via column chromatography then afforded the title compound as a colorless oil (17 g, 63.8% yield). LCMS: rt=1.79 min, [M-OH]+=265

Workup

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture was stirred at 50° C. for 2 h
  3. customPurification via column chromatography

Sources & evidence

ORD record
ord-9187d0d6a10244d9aade453254df0d76
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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