Hydrogen Peroxide → HCID 67776058, compound

HRID 705905Notes

Reaction equation

HRID 705905 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[CH3:17].B1C2CCCC1CCC2.[OH-:27].[Na+].OO>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:27])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH3:17]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 67775099HCID 67775099, compound

Product 1

HCID 67776058HCID 67776058, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 1-chloro-4-[(4-ethenylphenyl)oxy]-2-methylbenzene (2.46 g, 10.05 mmol) in dry THF (30 mL), was added 9-BBN (30.2 mL, 15.08 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (3 mL), followed by aq. NaOH (13.00 mL, 39.0 mmol), and 30% H2O2 (13.00 mL, 126 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 (1.13 g, 42.8% yield) as colorless oil. LCMS: rt=3.49 min, [M+H+]=245

Workup

  1. customquenched with water (3 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-db05dc54d0244e598baae307d3b63a77
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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