Hydrogen Peroxide → 2-(3-Fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenyl)ethanol

HRID 705924Notes

Reaction equation

HRID 705924 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([CH:19]=[CH2:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:10]=1.B1C2CCCC1CCC2.[OH-:30].[Na+].OO>C1COCC1>[F:1][C:2]1[CH:18]=[C:17]([CH2:19][CH2:20][OH:30])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[N:9][C:8]([C:11]([F:12])([F:13])[F:14])=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677766905-(2-Fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine

Product 1

HCID 677742942-(3-Fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenyl)ethanolYield 132%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 5-(2-fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine (540 mg, 1.900 mmol) in dry THF (8 mL), was added 9-BBN (5.70 mL, 2.85 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (1 mL), followed by aq. NaOH (2.5 mL, 7.50 mmol), and 30% H2O2 (2.585 g, 22.80 mmol). The reaction mixture was heated at 50° C. for 3 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 (756 mg, 2.501 mmol, 132% yield) as a white oil. LCMS: rt=3.63 min, [M+H+]=285

Workup

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

Sources & evidence

ORD record
ord-075dbcf6ed5d45729d759a47747a919b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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