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

HRID 2422681Notes

Reaction equation

HRID 2422681 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.[Cu](C#N)[C:13]#[N:14]>>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:13]#[N:14])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 2984702,5-Dibromo-3-nitropyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileYield 59%

Conditions

Temperature
150 °C

Procedure

2,5-Dibromo-3-nitropyridine (3.80 g, 13.4 mmol) and copper cyanide (2.42 g, 26.8 mmol) were mixed, and stirred under heat at 150° C. for 2 hours. After cooled to room temperature, the contents were filtered, and the residue was washed with acetone. The mother liquid was concentrated, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1) to obtain the intended compound (1.80 g, 59%) as a yellow solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationthe contents were filtered
  3. washthe residue was washed with acetone
  4. concentrationThe mother liquid was concentrated
  5. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1)

Sources & evidence

ORD record
ord-5f4cb9f67e6645d99dccb1313a9a85b4
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

Loading…