Sodium Cyanide → 3-(3-fluorophenyl)propanenitrile

Temperature

60 °C

3-Fluorophenethyl bromide (23, 1.00 g, 12.3 mmol) was diluted in dry DMF (25 mL). Sodium cyanide (1.06 g, 61.6 mmol) was added in one portion, and the mixture was heated to 60° C. under argon for 16 h. The mixture was cooled and concentrated, and the residue was partitioned between EtOAc and H2O (50 mL each). The layers were separated, and the aqueous phase was extracted with EtOAc (2×20 mL). The organic layers were washed with H2O and sat. aq. NaCl (50 mL each), dried over anhydrous sodium sulfate, and concentrated. The resulting oil was purified by flash column chromatography (SiO2), eluting with a gradient of 5% EtOAc in hexanes to 30% EtOAc in hexanes to yield the desired product as a colorless oil (0.638 g, 87%). 1H-NMR (500 MHz; CDCl3): δ 7.31 (td, J=7.9, 6.0 Hz, 1 H), 7.03-6.93 (m, 3 H), 2.96 (t, J=7.4 Hz, 2 H), 2.63 (t, J=7.4 Hz, 2 H).

1. temperatureThe mixture was cooled
2. concentrationconcentrated
3. customthe residue was partitioned between EtOAc and H2O (50 mL each)
4. customThe layers were separated
5. extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
6. washThe organic layers were washed with H2O and sat. aq. NaCl (50 mL each)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated
9. customThe resulting oil was purified by flash column chromatography (SiO2)
10. washeluting with a gradient of 5% EtOAc in hexanes to 30% EtOAc in hexanes

ORD record

ord-e888f39008f34601ba259c862562d6eb

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212144B2