Benzoyl Peroxide → 4-Nitrobenzyl bromide

HRID 1428773Notes

Reaction equation

HRID 1428773 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 74734-NitrotolueneHCID 67184N-bromobutanimide

Product 1

HCID 660114-Nitrobenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (1.51 g, 8.509 mmol) was added to a solution of 1-methyl-4-nitrobenzene (1.2 g, 7.735 mmol) in carbon tetrachloride. 70% benzoyl peroxide (cat. 120 mg) was added to the mixture at room temperature. The mixture was refluxed. After 24 h the mixture was extracted with ethyl acetate, dried over magnesium sulfate. Evaporation of the ethyl acetate and purification by column chromatography yielded 1-(bromomethyl)-4-nitrobenzene.

Workup

  1. temperatureThe mixture was refluxed
  2. extractionAfter 24 h the mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record
ord-161867770b7f412c89137ee129e0ca6a
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

Loading…