N-bromobutanimide → 1-Bromo-2-(bromomethyl)-3-nitrobenzene

HRID 2173266Notes

Reaction equation

HRID 2173266 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][Br:19]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1235372-Bromo-6-nitrotoluene

Product 1

HCID 150631701-Bromo-2-(bromomethyl)-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-bromo-2-methyl-3-nitrobenzene (50.0 g, 0.231 mol) in CCl4(500 mL) was added NBS (41.2 g, 0.231 mol) and BPO (6.51 g, 0.0231 mol), and the mixture was stirred at reflux for 1 h. Then the mixture was washed with 1 N HCl (300 mL*3), dried over Na2SO4, concentrated in vacuo. The residue was purified via chromatography (petrol ether) to give 1-bromo-2-(bromomethyl)-3-nitrobenzene.

Workup

  1. temperatureat reflux for 1 h
  2. washThen the mixture was washed with 1 N HCl (300 mL*3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via chromatography (petrol ether)

Sources & evidence

ORD record
ord-6d227a9eea8f4c6293fbc04d374f56bb
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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