Benzoyl Peroxide → 3-Bromo-2-(bromomethyl)pyridine

HRID 2264378Notes

Reaction equation

HRID 2264378 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:16])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]([CH2:8][Br:16])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 12010033-Bromo-2-methylpyridine

Product 1

HCID 214410813-Bromo-2-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 3-bromo-2-methylpyridine (46.5 g, 0.27 mol) in CCl4 (800 mL) was added NBS (53 g, 0.297 mol) and benzoylperoxide (4.7 g) and refluxed for 2 h in presence of light. The reaction mixture was cooled to 50° C. and filtered off the solid succinimide. The filtrate was concentrated and the crude 6-bromo-2-bromomethylpyridine was used for the follow-up reaction.

Workup

  1. temperaturerefluxed for 2 h in presence of light
  2. filtrationfiltered off the solid succinimide
  3. concentrationThe filtrate was concentrated
  4. customthe crude 6-bromo-2-bromomethylpyridine was used for the follow-up reaction

Sources & evidence

ORD record
ord-91b15969d53f42b7897bd17fc692702c
Source dataset
uspto-grants-2010_12
Patent number
US07855212B2

Reaction notes

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