Sodium borohydride → 3-(4-(4-Fluorophenoxy)phenyl)propanenitrile

Temperature

70 °C

To a solution of 3-(4-(4-fluorophenoxy)phenyl)acrylonitrile (5 g, 20.90 mmol) in ethanol (80 mL) was added NaBH4 (5.44 g, 144 mmol). The mixture was heated at 70° C. overnight. After cooling to room temperature, the reaction mixture was quenched with water (50 mL), and ethanol was removed under reduced pressure. The residue was partitioned between EA (100 mL) and water (50 mL). The organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL), dried over sodium sulfate, concentrated, and purified via flash chromatography to afford the title compound (4.7 g, 16.48 mmol, 79% yield) as a white solid. LCMS: rt=1.55 min, [M+H+]=242

1. temperatureAfter cooling to room temperature
2. customthe reaction mixture was quenched with water (50 mL), and ethanol
3. customwas removed under reduced pressure
4. customThe residue was partitioned between EA (100 mL) and water (50 mL)
5. washThe organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. custompurified via flash chromatography

ORD record

ord-7e5fe024895a4f99bd017d22ac356c71

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637536B2