Hydrogen Peroxide → 2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethanol

HRID 705835Notes

Reaction equation

HRID 705835 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)=[C:5]([F:21])[CH:4]=1)=[CH2:2].B1C2CCCC1CCC2.[OH-:31].[Na+].OO>C1COCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][OH:31])=[CH:4][C:5]=2[F:21])=[CH:11][C:12]=1[C:17]([F:20])([F:18])[F:19]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677746594-Chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2-fluorophenyl ether

Product 1

HCID 677742772-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethanolYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2-fluorophenyl ether (4.0 g, 12.63 mmol) in THF (13 mL) was added dropwise 9-BBN (50.5 mL, 25.3 mmol) at 0° C. The reaction mixture was stirred at room temperature for overnight, then mixed with NaOH (25.3 mL, 76 mmol) and H2O2 (7.74 mL, 76 mmol). The mixture was stirred at 55° C. for 4 h, quenched by Na2SO3, and extracted with EA (100 mL×3). Organic phases were collected, combined, dried with anhydrous Na2SO4, and concentrated to provide the title compound (4.02 g, 95% yield). LCMS: rt=4.6 min, [M+H+]=334

Workup

  1. stirringThe mixture was stirred at 55° C. for 4 h
  2. customquenched 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-a3c6fae769874b91be24d0554e18b7a3
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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