Benzoyl Peroxide → 2-(Bromomethyl)-4-nitropyridine

HRID 732996Notes

Reaction equation

HRID 732996 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 98849Pyridine, 2-methyl-4-nitro-

Product 1

HCID 218745752-(Bromomethyl)-4-nitropyridineYield 25%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-methyl-4-nitropyridine (1.79 g, 13.0 mmol) in CCl4 (30 mL) was treated with N-bromosuccinimide (2.31 g, 13.0 mmol) and benzoyl peroxide (420 mg, 1.30 mmol), stirred at 80° C. for 16 h, cooled to room temperature, filtered through Celite, concentrated in vacuo and purified by chromatography [SiO2; isohexane:EtOAc (15:1)] to give the title compound (700 mg, 25%) as a colourless oil; NMR δH (400 MHz, CDCl3) 8.89 (1H, d, J 5.0 Hz), 8.19 (1H, d, J 2.0 Hz), 7.96 (1H, dd, J 5.0, 2.0 Hz) and 4.66 (2H, s).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through Celite
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography [SiO2; isohexane:EtOAc (15:1)]

Sources & evidence

ORD record
ord-490d9c9cb4a644ca81c4a510d2d7854a
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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