Sodium Cyanide → 2-(4-Bromo-2-fluorophenyl)acetonitrile

Temperature

60 °C

To a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (500 g, 1.87 mol) in EtOH (2.2 L) stirred under nitrogen at 20° C. was added NaCN (93 g, 1.90 mmol) in one charge. The reaction mixture was stirred at 60° C. for 12 h. Then the solution was concentrated and distributed between DCM (2000 mL) and saturated NaHCO3 solution (1800 mL). Another batch was repeated using the same procedure. Then the two batches were combined. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated to provide 2-(4-bromo-2-fluorophenyl)acetonitrile (794 g, 99% yield): 1H NMR (400 MHz, CDCl3) δ 7.38-7.27 (m, 3H), 3.72 (s, 2H).

1. additioncharge
2. concentrationThen the solution was concentrated
3. extractionThe combined organic extract
4. washwas washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-4d26123450144f6c822740a1e4e87957

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382238B2