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

HRID 427513

Reaction equation

HRID 427513 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][Br:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 684723-Bromo-o-xylene

Product 1

HCID 133583181-Bromo-2-(bromomethyl)-3-methylbenzeneYield 45%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromo-o-xylene (15 g, 81 mmol), N-bromo succinimid (15.1 g, 85.1 mmol), dibenzoylperoxid (0.65 g) and tetrachloromethane (150 ml) was refluxed for 5 hours. After filtration the filtrate was washed with sodium hydrogensulfite and water. The organic layer was dried over sodium sulfate and evaporated in vacuo. Chromatography (SiO2) (petroleum ether:ethyl acetate, 100:4) gave a 16.8 g fraction of a mixture containing 45% of the title compound. This mixture was used without further purification.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationAfter filtration the filtrate
  3. washwas washed with sodium hydrogensulfite and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customChromatography (SiO2) (petroleum ether:ethyl acetate, 100:4) gave a 16.8 g fraction of a mixture

Sources & evidence

ORD record
ord-51db4384e25a49baa3d78657a3dfbb95
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Linked notes

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