Azobisisobutyronitrile → 3-Phenyl-2-chloro-6-bromomethylpyridine

HRID 363197Notes

Reaction equation

HRID 363197 reaction equation
[C:1]1([C:7]2[C:8]([Cl:14])=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2[C:8]([Cl:14])=[N:9][C:10]([CH2:13][Br:22])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 149805302-Chloro-6-methyl-3-phenylpyridine

Product 1

HCID 543404513-Phenyl-2-chloro-6-bromomethylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3-Phenyl-2-chloro-6-methylpyridine (0.094 g, 0.462 mmol), NBS (0.086 g, 0.485 mmol) and AIBN (0.008 g, 0.046mmol) in CCl4 (3 mL) were heated at reflux for 2 hours. The solvent was evaporated and the residue chromatographed (Silica gel, 100% CH2Cl2 to afford the title compound.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated
  3. customthe residue chromatographed (Silica gel, 100% CH2Cl2

Sources & evidence

ORD record
ord-6d7d8198179a4f568c3b52dbfa301801
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Reaction notes

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