Reaction #427162

Reaction equation

2,5-dibromo-3-methylpyridine

N,N-dimethylformamide

copper cyanide

→

desired product

Yield 49.4%

5-bromo-3-methylpyridine-2-carbonitrile

Yield 49.4%

Conditions

Workup

1. 1
   OtherThe reaction was partitioned between EtOAc and water
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Otherpurified by combi-flash chromatography

Procedure

To a solution of 2,5-dibromo-3-methylpyridine (5.0 g, 20. mmol) in N,N-dimethylformamide (20.0 mL, 259 mmol) was added copper cyanide (1.8 g, 20. mmol) and the reaction was stirred at 120° C. for 12 h. The reaction was partitioned between EtOAc and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated and purified by combi-flash chromatography to afford 1.94 g (49% yield) of the desired product as a white solid.

Source