2,5-Dibromo-3-nitropyridine → 5-Bromo-3-nitropyridine-2-carbonitrile

HRID 1404561Notes

Reaction equation

HRID 1404561 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[C:12]([Cu])#[N:13]>C(#N)CC.CCOC(C)=O>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:12]#[N:13])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 2984702,5-Dibromo-3-nitropyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileYield 86.6%

Reagents, catalysts & solvents 2

HCID 7854PropionitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2,5-dibromo-3-nitro-pyridine (25 g, 88.68 mmol) in propionitrile (100 ml) was added CuCN (8.7 g, 97.55 mmol) and the mixture was heated to 90° C. for 17 h. Then it was allowed to cool to room temperature, diluted with EtOAc, washed twice with brine, dried with Na2SO4 and concentrated. The remaining residue was purified by chromatography (silica gel; DCM/MeOH 95:5-85:15) to obtain the title compound as yellow solid (17.5 g, 68%).

Workup

  1. temperatureto cool to room temperature
  2. washwashed twice with brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe remaining residue was purified by chromatography (silica gel; DCM/MeOH 95:5-85:15)

Sources & evidence

ORD record
ord-cb2040b0e11c4c02980b3ef2596a3d2c
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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