3,5-Dibromo-4-methylpyridine → 5-Bromo-4-methylpyridine-3-carbonitrile
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[CH3:8].[Cu](C#N)[C:11]#[N:12]>CN(C)C=O>[Br:9][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:7]=1[CH3:8])[C:11]#[N:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a stirred solution of 3,5-dibromo-4-methylpyridine (2.0 g, 7.97 mmol) in dry N,N-dimethylformamide (10 mL) was added copper cyanide (1.07 g, 11.95 mmol) at room temperature. The reaction mixture was heated at 150° C. for 6 h, cooled it, quenched with water (5 mL) and extracted with 50% ethyl acetate/hexane (2×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. MS (M+1): 199.1.
Workup
- temperaturecooled it
- customquenched with water (5 mL)
- extractionextracted with 50% ethyl acetate/hexane (2×100 mL)
- washThe combined organic layer was washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulphate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-42aa259a33df4b999ab848117ad309b7
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073929B2
Reaction notes
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