Ammonia → 3-Bromo-5-methylbenzonitrile
Reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.[Cu](C#N)[C:11]#[N:12].N1C=CC=CC=1.N>O.CN(C=O)C>[Br:9][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH3:8])[CH:5]=1)[C:11]#[N:12]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 190 °C
Procedure
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+.
Workup
- temperatureto cool to r.t.
- extractionthe water phase was extracted with EtOAc
- dry with materialThe combined organic extracts were dried (Mg2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatograpy (hexane/EtOAc gradient elution)
Sources & evidence
- ORD record
- ord-8e49b62fc51948bd9a5416a7fe9d0eec
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865911B2
Reaction notes
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