Potassium Cyanide → 2-(4-Bromo-3-fluorophenyl)acetonitrile

Temperature

60 °C

To a solution of 1-bromo-4-(bromomethyl)-2-fluorobenzene (1 g, 3.73 mmol) in EtOH (30 mL) was added KCN (0.243 g, 3.73 mmol). The resulting mixture was stirred at 60° C. After 3 h, LCMS analysis showed the starting material had disappeared. The solvent was removed in vacuo. The residue was dissolved in EA (80 mL) was washed with H2O (30 mL) and brine (30 mL). The organic layer was dried and concentrated to give the crude product, which was purified by silica column chromatography (PE/EA=10/1) to yield a white solid of 2-(4-bromo-3-fluorophenyl)acetonitrile (0.78 g, 2.96 mmol, 79.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.63 (t, J=7.8 Hz, 1H), 7.24 (d, J=9.2 Hz, 1H), 7.12 (d, J=9.6 Hz, 1H), 3.92 (s, 2H); ES-LCMS m/z 214.0 (M+H).

1. customThe solvent was removed in vacuo
2. dissolutionThe residue was dissolved in EA (80 mL)
3. washwas washed with H2O (30 mL) and brine (30 mL)
4. customThe organic layer was dried
5. concentrationconcentrated
6. customto give the crude product, which
7. customwas purified by silica column chromatography (PE/EA=10/1)

ORD record

ord-2bcbb15271334ff899a5b77fce2ea0cf

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382238B2