Benzyl Alcohol → 2-(Benzyloxy)-6-fluoropyridine

Temperature

50 °C

Benzylalcohol (1.88 g, 17.38 mmol) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 458 mg, 19.11 mmol) in tetrahydrofuran (15 mL) and the mixture was heated to 50° C. for 45 minutes. The reaction mixture was then cooled to room temperature, a solution of 2,6-difluoropyridine (2 g, 17.38 mmol) in tetrahydrofuran (4 mL) was added dropwise and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was then diluted with ethyl acetate, concentrated in vacuo and the residue was partitioned between ethyl acetate (50 mL) and water (20 mL). The organic layer was separated, washed with brine (20 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was then concentrated in vacuo from dichloromethane to afford the title compound as a clear oil in 98% yield, 3.48 g. LRMS APCI m/z 204 [M+H]+.

1. temperatureThe reaction mixture was then cooled to room temperature
2. concentrationconcentrated in vacuo
3. customthe residue was partitioned between ethyl acetate (50 mL) and water (20 mL)
4. customThe organic layer was separated
5. washwashed with brine (20 mL)
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. concentrationThe residue was then concentrated in vacuo from dichloromethane

ORD record

ord-57f3f031903949519cc56db8f6586425

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394278B2