Hydrogen Peroxide → 2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanol

Participants

Reaction Steps

To a mixture of 1-chloro-4-[(4-ethenylphenyl)oxy]-2-(trifluoromethyl)benzene (3.8 g, 12.72 mmol) in anhydrous tetrahydrofuran (50 mL) was added 9-BBN (50.9 mL, 25.4 mmol) dropwise at 0° C. The reaction mixture was stirred at rt overnight, then sodium hydroxide (42.4 mL, 127 mmol) and H2O2 (2.60 mL, 25.4 mmol) were added at 0° C. The reaction mixture was stirred for 2 h at 50° C., and quenched with aq. Na2SO3 and then concentrated. Purification via mass-directed auto-preparation afforded the title compound (2.0 g).

Provenance & Evidence