Hydrogen Peroxide → 2-{4-[(3-Fluoro-4-methylphenyl)oxy]phenyl}ethanol

To the solution of 4-ethenylphenyl 3-fluoro-4-methylphenyl ether (900 mg, 3.94 mmol) in dry THF (30 mL), was added 9-BBN (9.46 mL, 4.73 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (1.2 mL), followed by aq. NaOH (5.26 mL, 15.77 mmol), and 30% H2O2 (4.03 mL, 39.4 mmol). The reaction mixture was heated at 50° C. for 2 h. Then THF was removed under reduced pressure, and the residue was diluted with DCM. 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 (1.02 g, 4.14 mmol, 105% yield) as a yellow oil. LCMS: rt=3.29 min, [M+H]=229

1. customquenched with water (1.2 mL)
2. temperatureThe reaction mixture was heated at 50° C. for 2 h
3. customThen THF was removed under reduced pressure
4. additionthe residue was diluted with DCM
5. washThe organic layer was washed with water and brine
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated
8. custompurified by flash chromatography

ORD record

ord-80a43c053ad742eaa3e3222702b08187

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174968B2