Azobisisobutyronitrile → 2-Bromo-4-(bromomethyl)pyridine

HRID 279599Notes

Reaction equation

HRID 279599 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][Br:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27340872-Bromo-4-methylpyridine

Product 1

HCID 129548062-Bromo-4-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-bromo-4-methylpyridine (12.2 g), N-bromosuccinimide (30 g) and 2,2′-azobis(2-methylpropionitrile) (100 mg) in carbon tetrachloride (200 ml) was heated at reflux for 2.5 hours. The mixture was allowed to cool and the insoluble material removed by filtration. The solvent was removed from the filtrate by evaporation and the residue was purified by filtration through a silica pad eluting with ethyl acetate/hexane (10/1) to give 2-bromo-4-bromomethylpyridine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureto cool
  4. customthe insoluble material removed by filtration
  5. customThe solvent was removed from the filtrate by evaporation
  6. filtrationthe residue was purified by filtration through a silica pad
  7. washeluting with ethyl acetate/hexane (10/1)

Sources & evidence

ORD record
ord-71c6379b5a0e40a0ae01413bbc991edc
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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