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

Participants

Reaction Steps

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

Provenance & Evidence