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

HRID 1384613Notes

Reaction equation

HRID 1384613 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. 1H NMR Spectrum: (DMSOd6) 4.65(s, 2H); 7.50(d, 1H); 7.42(s, 1H); 7.70(s, 1H); 8.35(d, 1H) MS-ESI: 250 [MH]+

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-cc30c2f544c84955a8184dc40bdfce1c
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

Loading…