Azobisisobutyronitrile → 3,5-Dibromo-2-(bromomethyl)pyridine

HRID 2224349

Reaction equation

HRID 2224349 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C1C(=O)N([Br:17])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:9][Br:17])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 6197053,5-Dibromo-2-methylpyridine

Product 1

HCID 534171773,5-Dibromo-2-(bromomethyl)pyridineYield 55%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 52A (1.25 g, 4.98 mmol) in CCl4 (7 ML) was added NBS (0.89 g, 4.98 mmol) followed by catalytic AIBN and the mixture was heated to reflux for 4 hours. The reaction was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 10% CH2Cl2/Hexane then 50% CH2Cl2/Hexane) to give 52B (0.90 g, 55%). HPLC Rt=2.85 min.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2, 10% CH2Cl2/Hexane

Sources & evidence

ORD record
ord-989c30392564450eb7b6d497f16e4150
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Linked notes

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