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

HRID 911421Notes

Reaction equation

HRID 911421 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)pyridineYield 45.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a mixture of 3-bromo-2-methylpyridine (J. Med. Chem. 1987, 30, 871-880) (2.7 g, 15.8 mmol), NBS (3.10 g, 17.42 mmol), and benzoyl peroxide (190 mg, 0.78 mmol) in carbon tetrachloride (50 mL) overnight at 85° C. Cool to ambient temperature, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting with toluene to provide the title compound as a white solid (1.81 g, 45%).

Workup

  1. temperatureHeat
  2. filtrationfilter
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with toluene

Sources & evidence

ORD record
ord-9dfba7d11bdc40868102fbc599d8adef
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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