Hydrogen Peroxide → HCID 67775185, compound

HRID 705889Notes

Reaction equation

HRID 705889 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=2)[N:4]=1.B1C2CCCC1CCC2.[OH-:29].[Na+].OO>C1COCC1>[F:19][C:2]([F:1])([F:18])[C:3]1[N:4]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:29])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 67775614HCID 67775614, compound

Product 1

HCID 67775185HCID 67775185, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 2-(trifluoromethyl)-6-(4-vinylphenoxyl)pyridine (2.4 g, 9.05 mmol) in dry THF (25 mL), was added 9-BBN (30 ml, 15.00 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (2 mL), followed by aq. NaOH (12 mL, 36.0 mmol), and 30% H2O2 (12 mL). The reaction mixture was heated at 50° C. for 1 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 (3.68 g, 8.44 mmol, 93% yield) as a white oil. LCMS: rt=3.00 min, [M+H+]=284

Workup

  1. customquenched with water (2 mL)
  2. temperatureThe reaction mixture was heated at 50° C. for 1 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-0b02267b61084cacabe3154fa9eca932
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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