Benzoyl Peroxide → 5-Bromo-2-(bromomethyl)pyridine

HRID 1435868Notes

Reaction equation

HRID 1435868 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N: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[CH:3]=[CH:4][C:5]([CH2:8][Br:16])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 12010205-Bromo-2-methylpyridine

Product 1

HCID 234380625-Bromo-2-(bromomethyl)pyridineYield 93.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 5-bromo-2-methylpyridine (1.2 g, 4.78 mmole), in dry CCl4 (150 mL) at RT was added NBS (1.02 g, 5.73 mmole) and benzoylperoxide (0.12 g, 0.48 mmole). After 18 h at reflux, the reaction contents were cooled to RT and filtered through a scintered-glass funnel washing with CHCl3. Concentration under vacuum and purification on silica (EtOAc) afforded the title compound (1.12 g, 71%) as light yellow solid: (EtOAc): LC-MS (ES) m/e 330 (M)+.

Workup

  1. temperatureAfter 18 h at reflux
  2. customthe reaction contents
  3. filtrationfiltered through a scintered-glass funnel
  4. washwashing with CHCl3
  5. concentrationConcentration
  6. customunder vacuum and purification on silica (EtOAc)

Sources & evidence

ORD record
ord-b9726918d882443fb5df818e22261f6c
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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