tert-Butyl peroxybenzoate → 1-Bromo-3-(bromomethyl)-5-methylbenzene

HRID 1432106Notes

Reaction equation

HRID 1432106 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(C)(C)C>ClC(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9][Br:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11966tert-Butyl peroxybenzoateHCID 67184N-bromobutanimideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5 ml (36.8 mmol) 5-bromo-m-xylene and 6.55 g (36.8 mmol) N-bromo-succinimide in 35 ml tetrachloromethane is added 0.138 ml (0.74 mmol) tert-butyl-perbenzoate. The mixture is irradiated using a heating lamp and stirred for 3 hrs at reflux temperature. The mixture is cooled to room temperature, filtered and evaporated. The product is isolated by chromatography on silica gel (flashmaster, hexane) to give the title compound as white crystals.

Workup

  1. customThe mixture is irradiated
  2. temperatureat reflux temperature
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is isolated by chromatography on silica gel (flashmaster, hexane)

Sources & evidence

ORD record
ord-b0131a1093db4b5183141c7811f11b27
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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