Benzoyl Peroxide → 1-Bromo-3-(bromomethyl)-2-chlorobenzene

HRID 577042Notes

Reaction equation

HRID 577042 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[Cl:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Br:10])[C:3]=1[Cl:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 133481341-Bromo-2-chloro-3-methylbenzene

Product 1

HCID 223242561-Bromo-3-(bromomethyl)-2-chlorobenzeneYield 46%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-bromo-2-chloro-3-methylbenzene (10 g, 48.7 mmol) was dissolved in CCl4 (100 mL), and then N-bromosuccinimide (13.0 g, 73.0 mmol) and benzoyl peroxide (5.9 g, 24.3 mmol) were added. The mixture was stirred for 2 hours at reflux. The solid was removed by filtration, and the filtrate was washed with water and dried over sodium sulfate. After evaporation of the solvent, the residue was dissolved in DCM and purified on silica gel using 10% hexane/AcOEt to afford 1-bromo-3-(bromomethyl)-2-chlorobenzene (6.36 g, 46% yield); 1H NMR (400 MHz, CDCl3): δ 4.62 (s, 2H), 7.12 (t, J=7.8 Hz, 1H), 7.39 (dd, J=1.6 Hz, J=7.6 Hz, 1H), 7.60 (dd, J=1.6 Hz, J=8.0 Hz, 1H).

Workup

  1. temperatureat reflux
  2. customThe solid was removed by filtration
  3. washthe filtrate was washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 10% hexane/AcOEt

Sources & evidence

ORD record
ord-969e83e057e34b4e93d2bf993e49f5b1
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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