Hydrogen Peroxide → 2-(4-(4-Chloro-2,6-difluorophenoxy)phenyl)ethanol

HRID 705932Notes

Reaction equation

HRID 705932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:18])[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=2)=[C:6]([F:8])[CH:7]=1.B1C2CCCC1CCC2.[OH-:28].[Na+].OO>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([F:18])[C:5]([O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][OH:28])=[CH:14][CH:15]=2)=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 67774918HCID 67774918, compound

Product 1

HCID 677756402-(4-(4-Chloro-2,6-difluorophenoxy)phenyl)ethanolYield 57.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 5-chloro-1,3-difluoro-2-(4-vinylphenoxyl)benzene (2.6 g, 9.75 mmol) in dry THF (10 mL), was added 9-BBN (39.0 mL, 19.50 mmol) at 0° C. The mixture was stirred at room temperature overnight. aq. NaOH (7.0 mL, 21.00 mmol), and 30% H2O2 (2.0 mL, 19.58 mmol) were added then. The reaction mixture was heated at 50° C. for 4 h. Then THF was removed under reduced pressure, and the residue was diluted with EA. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated and purified by flash chromatography to afford the title compound (1.6 g, 5.62 mmol, 57.6% yield) as a white oil.

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 4 h
  2. customThen THF was removed under reduced pressure
  3. additionthe residue was diluted with EA
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-cd6607e4ab5344ae8c3364d2f58156b7
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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