Ethyl Acetate → 5-Bromo-4-methylpyridine-3-carbonitrile

HRID 1502031Notes

Reaction equation

HRID 1502031 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]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8193383,5-Dibromo-4-methylpyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 70606815-Bromo-4-methylpyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperaturewas refluxed for 4 hours
  2. temperaturebefore cooled down
  3. customthe precipitate was removed by filtration
  4. washThe filtrate was washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. 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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