Azobisisobutyronitrile → 2-Bromo-5-bromomethylpyridine

HRID 2422371Notes

Reaction equation

HRID 2422371 reaction equation
CC1C=CC(Br)=NC=1.BrN1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36](Br)[Br:37])=[CH:32][N:31]=1>C(Cl)(Cl)(Cl)Cl>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][Br:37])=[CH:32][N:31]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5642162-Bromo-5-methylpyridine2×HCID 566051432-Bromo-5-(dibromomethyl)pyridine

Product 1

HCID 64246602-Bromo-5-bromomethylpyridineYield 43%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred slurry of 10.320 g (60.0 mmol) of 5-methyl-2-bromopyridine and 5.339 g (30.0 mmol, 0.5 eq) of recrystallized N-bromosuccinimide in 150 mL of carbon tetrachloride was added 200 mg of AIBN. The reaction mixture was purged twice with argon and evacuated and set to reflux under argon. After 90 min, the reaction mixture was cooled to room temperature, filtered and the filtrate concentrated to give a yellow oil. Proton NMR indicated that the mixture contains 53% (mol) unreacted 5-methyl-2-bromopyridine, 43% of the title product and 4% of 2-bromo-5-(dibromomethyl)pyridine. The mixture was used immediately without further purification for the following procedure.

Workup

  1. customThe reaction mixture was purged twice with argon
  2. customevacuated
  3. temperatureto reflux under argon
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-ad05b86238b541e1931ca973a54c55d2
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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