Ammonia → 3-Bromo-5-methylbenzonitrile

Temperature

190 °C

A mixture of 1,3-dibromo-5-methylbenzene (1.0 g, 4.0 mmol), copper cyanide (0.179 g, 2.00 mmol), pyridine (0.323 mL, 4.00 mmol), and DMF (15 mL) were heated at 190° C. for 10 h in microwave reactor. The reaction mixture was allowed to cool to r.t., and then poured into a solution of H2O (20 mL) and aq. NH3 solution (25-35% NH3, 10 mL) and the water phase was extracted with EtOAc. The combined organic extracts were dried (Mg2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatograpy (hexane/EtOAc gradient elution) to afford the title compound (0.58 g, 74% yield): 1H NMR (500 MHz, CDCl3) δ ppm 2.39 (s, 3 H) 7.41 (s, 1 H) 7.58 (s, 1 H) 7.60 (s, 1 H); MS (EI) m/z 195 M

1. temperatureto cool to r.t.
2. extractionthe water phase was extracted with EtOAc
3. dry with materialThe combined organic extracts were dried (Mg2SO4)
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel chromatograpy (hexane/EtOAc gradient elution)

ORD record

ord-6aa3c734c0c8438e8c338e845cf82a60

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415483B2