Hydrogen Peroxide → 3,5-Difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde

HRID 474690Notes

Reaction equation

HRID 474690 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([CH:19]=C)[CH:16]=[C:15]([F:21])[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-:31].[Na+].OO>C1COCC1>[F:1][C:2]1[CH:18]=[C:17]([CH:16]=[C:15]([F:21])[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)[CH:19]=[O:31]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677743945-(2,6-Difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine

Product 1

HCID 866662153,5-Difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehydeYield 153%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 5-(2,6-difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine (1.67 g, 5.53 mmol) in dry THF (25 mL), was added 9-BBN (20 ml, 10.00 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (2 mL), followed by aq. NaOH (7 mL, 21.0 mmol), and 30% H2O2 (7 mL, 5.53 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 (2.7 g, 8.43 mmol, 153% yield) as a white oil. LCMS: rt=2.97 min, [M+H+]=321

Workup

  1. customquenched with water (2 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-3f0a2d40f9974bbaa14f5a449cc54089
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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