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-a02d9b890698412da6e1b59facda3dbc

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207198B2