Hydrogen Peroxide → HCID 67773911, compound

HRID 474692Notes

Reaction equation

HRID 474692 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[O:17][C:18]([F:21])([F:20])[F:19].B1C2CCCC1CCC2.[OH-:31].[Na+].OO>C1COCC1>[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:31])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[O:17][C:18]([F:20])([F:19])[F:21]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 67776822HCID 67776822, compound

Product 1

HCID 67773911HCID 67773911, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 1-chloro-2-(trifluoromethoxy)-4-(4-vinylphenoxy)benzene (1.2 g, 3.81 mmol) in dry THF (10 mL), was added 9-BBN (15.25 mL, 7.63 mmol) at 0° C. The mixture was stirred at room temperature overnight. aq. NaOH (6.5 mL, 19.50 mmol), and 30% H2O2 (2.0 mL, 19.58 mmol) were added. The reaction mixture was heated at 55° 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 (450 mg, 1.353 mmol, 35.5% yield) as a white oil.

Workup

  1. temperatureThe reaction mixture was heated at 55° 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-0e743f1bbcbb41da8edeab6d383a173b
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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