Water → 5-Bromopyridine-2-carbonitrile

HRID 1966924Notes

Reaction equation

HRID 1966924 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C-:9]#[N:10].[C-]#N.[Na+].O>CN(C)C=O>[C:9]([C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1)#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 5975CyanideHCID 8929Sodium CyanideHCID 693532,5-Dibromopyridine

Product 1

HCID 8171545-Bromopyridine-2-carbonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

In 1 L of dimethylformamide was dissolved 100 g of 2,5-dibromopyridine, 32 g of cupper cyanide and 17.8 g of sodium cyanide were added to the solution at room temperature and the solution was stirred at the temperature of 150° C. for 7 hours for reaction. After being cooled to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dehydrated, filtered and concentrated in vacuo. The title compound 54 g was obtained. Yield 70%.

Workup

  1. additionwere added to the solution at room temperature
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38f6ad651de54c488c9f8df9ad99d8d8
Source dataset
uspto-grants-2013_04
Patent number
US08420676B2

Reaction notes

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