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

HRID 705876Notes

Reaction equation

HRID 705876 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

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 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 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-chloro-2-(trifluoromethyl)-4-(4-vinylphenoxyl)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

  1. temperatureto warm up to room temperature
  2. temperatureThe mixture was then heated at 60° C. for 2 h
  3. customto quench
  4. customthe reaction
  5. temperatureafter cooling
  6. customPurification via flash chromatography

Sources & evidence

ORD record
ord-c97fc9d0aa4d4dde97e816bffd6dcc61
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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