Benzoyl Peroxide → 3-Bromo-2-(bromomethyl)pyridine
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureHeat
- filtrationfilter
- concentrationconcentrate in vacuo
- 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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