Azobisisobutyronitrile → 2-Pyridinecarboxylic acid, 3-(bromomethyl)-6-chloro-, methyl ester

HRID 1799555Notes

Reaction equation

HRID 1799555 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[CH:4][CH:3]=1.C1C(=O)N([Br:20])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:5]1[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 45489870Methyl 6-chloro-3-methylpyridine-2-carboxylate

Product 1

HCID 582166312-Pyridinecarboxylic acid, 3-(bromomethyl)-6-chloro-, methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 6-chloro-3-methylpyridine-2-carboxylate (3.46 g, 18.6 mmol), NBS (3.32 g, 18.6 mmol) and AIBN (61 mg, 0.37 mmol) were stirred in refluxing CCl4 (40 mL) for 6 hours. The mixture was then cooled to room temperature and purified directly by silica gel chromatography (2-20% EtOAc/hexanes) to give the title compound as a white solid.

Workup

  1. custompurified directly by silica gel chromatography (2-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-02b2e190108246de90eb1079c090545b
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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