Hydrogen Peroxide → 2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-(2-hydroxyethyl)benzonitrile

HRID 705879Notes

Reaction equation

HRID 705879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH:17]=[CH2:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].B1C2CCCC1CCC2.[OH2:32].[OH-].[Na+].OO>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:32])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 66825615HCID 66825615, compound

Product 1

HCID 668256932-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-(2-hydroxyethyl)benzonitrileYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-ethenylbenzonitrile (2.0 g, 6.18 mmol) in dry THF (14 mL), was added 9-BBN (18 mL, 9.00 mmol) at 0° C. The mixture was stirred at room temperature overnight. Water (1.113 mL, 61.8 mmol), aq. NaOH (12.36 mL, 37.1 mmol), and 30% H2O2 (3.16 mL, 30.9 mmol) were added then. 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 (1.0 g, 2.93 mmol, 47.4% yield).

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-48cfe8516571453397e907311d883385
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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