Hydrogen Peroxide → HCID 86666194, compound

HRID 474589Notes

Reaction equation

HRID 474589 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([F:9])[C:6]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=2)=[C:5]([F:22])[CH:4]=1)=[CH2:2].B1C2CCCC1CCC2.[OH-:32].[Na+].OO>C1COCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:6]2[C:5]([F:22])=[CH:4][C:3]([CH2:1][CH2:2][OH:32])=[CH:8][C:7]=2[F:9])=[CH:12][C:13]=1[C:18]([F:19])([F:21])[F:20]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86666195HCID 86666195, compound

Product 1

HCID 86666194HCID 86666194, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2,6-difluorophenyl ether (3.2 g, 9.56 mmol) in THF (10 mL) was added dropwise 9-BBN (38.2 mL, 19.12 mmol) at 0° C. The reaction mixture was stirred at room temperature for overnight. It was mixed with NaOH (19.12 mL, 57.4 mmol) and H2O2 (5.86 mL, 57.4 mmol), the mixture was stirred at 55° C. for 4 h. It was quenched by Na2SO3 and extracted with EA (100 ml×3). Organic phases were collected, combined, dried with anhydrous Na2SO4, and concentrated to afford the title compound (3.10 g, 92% yield). LCMS: rt=4.72 min, [M+H+]=352

Workup

  1. stirringthe mixture was stirred at 55° C. for 4 h
  2. customIt was quenched by Na2SO3
  3. extractionextracted with EA (100 ml×3)
  4. customOrganic phases were collected
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22a3d6558c5f40489c2eedd4c2cc2e26
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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