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

HRID 920320Notes

Reaction equation

HRID 920320 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-:30].[Na+].OO>O1CCCC1>[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:30])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:17]([F:18])([F:19])[F:20]

Participants

6

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 49.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-chloro-4-[(4-ethenylphenyl)oxy]-2-(trifluoromethyl)benzene (3.8 g, 12.72 mmol) in anhydrous tetrahydrofuran (50 mL) was added 9-BBN (50.9 mL, 25.4 mmol) dropwise at 0° C. The reaction mixture was stirred at rt overnight, then sodium hydroxide (42.4 mL, 127 mmol) and H2O2 (2.60 mL, 25.4 mmol) were added at 0° C. The reaction mixture was stirred for 2 h at 50° C., and quenched with aq. Na2SO3 and then concentrated. Purification via mass-directed auto-preparation afforded the title compound (2.0 g).

Workup

  1. stirringThe reaction mixture was stirred for 2 h at 50° C.
  2. customquenched with aq. Na2SO3
  3. concentrationconcentrated
  4. customPurification
  5. customvia mass-directed auto-preparation

Sources & evidence

ORD record
ord-5018a6f5801d4fe99b29ca39bf130ebc
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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