Benzoyl Peroxide → 2-(Bromomethyl)-3-nitropyridine
Reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][C:28]1[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[CH:30][N:29]=1.BrBr>ClC1C=CC=CC=1>[Br:1][CH2:27][C:28]1[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[CH:30][N:29]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
51 g (290 mmol) of N-bromosuccinimide and 0.5 g of benzoyl peroxide were added, a little at a time, to a mixture of 40 g (290 mmol) of 2-methyl-3-nitropyridine (Example 3.b) and 400 ml of chlorobenzene, at the boiling point (liberation of bromine). After approximately 2 hours, the reaction mixture was cooled to room temperature (approximately 25° C.) and filtered, and the resulting solution was freed from solvent under reduced pressure. The resulting residue was chromatographed twice (cyclohexane/methylene chloride; cyclohexane/ethyl acetate). This gave 10.4 g (17%) of the title compound as a yellow oil.
Workup
- filtrationfiltered
- customThe resulting residue was chromatographed twice (cyclohexane/methylene chloride; cyclohexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-089558da0d474d69851dc45421b065c9
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977146
Reaction notes
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