Benzoyl Peroxide → 3-Bromo-2-(bromomethyl)-6-methoxy-4-methylpyridine

HRID 1043907Notes

Reaction equation

HRID 1043907 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[N:4][C:5]([O:9][CH3:10])=[CH:6][C:7]=1[CH3:8].C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:11][Br:19])=[N:4][C:5]([O:9][CH3:10])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 112413813-Bromo-6-methoxy-2,4-dimethylpyridine

Product 1

HCID 866863403-Bromo-2-(bromomethyl)-6-methoxy-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromo-6-methoxy-2,4-dimethylpyridine obtained in Preparation Example 22 (200 mg), NBS (165 mg) and benzoyl peroxide (6.73 mg) was heated under reflux in a carbon tetrachloride solvent (4 mL) for two hours. The reaction mixture was cooled to room temperature and then filtered. The resulting filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 5%) to give the title compound (126 mg).

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. concentrationThe resulting filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 5%)

Sources & evidence

ORD record
ord-590b71fa388c4a8fa285bcde42713374
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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