Azobisisobutyronitrile → 6-(Bromomethyl)pyridine-3-carbonitrile

HRID 1355597Notes

Reaction equation

HRID 1355597 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[Br:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 2819956-Methylpyridine-3-carbonitrile

Product 1

HCID 219277766-(Bromomethyl)pyridine-3-carbonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-Methylnicotinonitrile (11-1) (Lancaster) (15 g, 127 mmol) in carbon tetrachloride (300 ml) was added N-bromosuccinimide (27.12 g, 152.4 mmol). The resulting solution was degassed and purged with nitrogen and AIBN (2,2′-azobisisobutyronitrile) (2.08 g, 12.6 mmol) was added. After 7 hours at 85° C., another batch of AIBN (1.04 g) was added and stirring was continued for another hour. After removal of the solvent the crude product was subjected to flash column chromatography in ethylacetate/hexanes to yield 10 g pure material (40%).

Workup

  1. customThe resulting solution was degassed
  2. additionwas added
  3. waitwas continued for another hour
  4. customAfter removal of the solvent the crude product

Sources & evidence

ORD record
ord-c5db397043284f1784533932ba5de40c
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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