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

HRID 1737562Notes

Reaction equation

HRID 1737562 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-d3f1ec21f5564f889b1fefcd6f4e98a6
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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