Ethyl Acetate → 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].[C:10]([Cu])#[N:11].CCOC(C)=O>CN(C=O)C>[Br:9][C:6]1[C:7]([CH3:8])=[C:2]([C:10]#[N:11])[CH:3]=[N:4][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3,5-dibromo-4-methylpyridine (16 g, 64 mmol) and CuCN (6.2 g, 69 mmol) in 150 mL of DMF was refluxed for 4 hours before cooled down. The reaction mixture was poured to 1 L of EtOAc with stirring and the precipitate was removed by filtration. The filtrate was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to afford 5-bromo-4-methylpyridine-3-carbonitrile.
Workup
- temperaturewas refluxed for 4 hours
- temperaturebefore cooled down
- customthe precipitate was removed by filtration
- washThe filtrate was washed with water, brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-5de5469c8b0e4c90afecc837e125c4d2
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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