Azobisisobutyronitrile → 5-(Bromomethyl)pyridine-2-carbonitrile

HRID 1672757Notes

Reaction equation

HRID 1672757 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][N:4]=1)#[N:2].[Br:10]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl>[Br:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 741835-Methylpicolinonitrile

Product 1

HCID 219277275-(Bromomethyl)pyridine-2-carbonitrileYield 53.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Commercially available 2-cyano-5-methylpyridine (1.90 g, 16.1 mmol) was dissolved in chloroform (100 mL), and the mixture was stirred at 60° C. for 6 hours after adding N-bromosuccinimide (4.29 g, 24.1 mmol) and α,α-azobisisobutyronitrile (0.792 g, 4.82 mmol). After ice-cooling the reaction mixture, the precipitate was separated by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 5-bromomethyl-2-cyanopyridine (1.69 g, 53%).

Workup

  1. temperatureAfter ice-cooling the reaction mixture
  2. customthe precipitate was separated by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53e68ec02d4f41afaa5e0fafb0d63ce0
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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