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

HRID 705805Notes

Reaction equation

HRID 705805 reaction equation
B1C2CCCC1CCC2.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH2:25])=[CH:20][CH:19]=2)=[CH:13][C:12]=1[C:26]([F:29])([F:28])[F:27].[OH-:30].[Na+].OO>C1COCC1.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][OH:30])=[CH:22][CH:23]=2)=[CH:13][C:12]=1[C:26]([F:27])([F:28])[F:29]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 668258371-Chloro-2-(trifluoromethyl)-4-(4-vinylphenoxy)benzene

Product 1

HCID 668255292-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanolYield 71.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

9-BBN (158 mL, 79 mmol) was added to a solution of 1-chloro-2-(trifluoromethyl)-4-(4-vinylphenoxyl)benzene (15.75 g, 52.7 mmol) in THF (160 mL) at 0° C. The resultant reaction mixture was stirred at room temperature overnight. To the mixture was added water (16 mL), 3M NaOH solution (80 mL) and 30% hydrogen peroxide (80 mL). It was stirred at 50° C. for 2 h, concentrated in vacuo, and diluted with ethyl acetate (200 mL). The organic phase was collected, washed with water (100 mL×2) & brine (100 mL), dried over sodium sulfate, and concentrated. Purification via a column chromatography then provided the title compound as a colorless oil (12.13 g, 71.7% yield). LCMS: rt=2.08 min, [M+H+]=299

Workup

  1. customThe resultant reaction mixture
  2. stirringIt was stirred at 50° C. for 2 h
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate (200 mL)
  5. customThe organic phase was collected
  6. washwashed with water (100 mL×2) & brine (100 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification via a column chromatography

Sources & evidence

ORD record
ord-ae5b93274d9842e4ab95ca6863d52136
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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