Azobisisobutyronitrile → 1-Bromo-3-(bromomethyl)-2-chlorobenzene

HRID 1042355Notes

Reaction equation

HRID 1042355 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[Cl:9].C1C(=O)N([Br:17])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Br:17])[C:3]=1[Cl:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 133481341-Bromo-2-chloro-3-methylbenzene

Product 1

HCID 223242561-Bromo-3-(bromomethyl)-2-chlorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1-bromo-2-chloro-3-methyl-benzene (3.90 g, 19.00 mmol), NBS (3.60 g, 20.20 mmol) and a catalytic amount of AIBN (50 mg) in CCl4 was refluxed for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The precipitate was washed with pentane. The solvent was distilled off and the residue was purified by column chromatography using pentane as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 4.62 (s, 2H), 7.14 (t, J=7.62 Hz, 1H), 7.39 (dd, J=7.62 Hz, 1H), 7.60 (dd, J=7.91 Hz, 1H).

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed with pentane
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-769e8720fd494b18bcc6b7db6e6beb3c
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

Loading…