Benzoyl Peroxide → 1-Bromo-4-(bromomethyl)-2-chlorobenzene

HRID 1930169Notes

Reaction equation

HRID 1930169 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=1[Cl:27].[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][Br:28])=[CH:22][C:21]=1[Cl:27]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1387894-Bromo-3-chlorotoluene

Product 1

HCID 129473921-Bromo-4-(bromomethyl)-2-chlorobenzeneYield 94.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Benzoic peroxyanhydride (3.73 g, 15.41 mmol) was added to a degassed mixture of 1-bromo-2-chloro-4-methylbenzene (24.35 g, 118.50 mmol) and 1-bromopyrrolidine-2,5-dione (23.20 g, 130.35 mmol) in CCl4 (100 mL) at room temperature under nitrogen. The resulting mixture was stirred at reflux for 18 hrs. The reaction was cooled and washed with water (equal volume); satd sodium thiosulfite (equal volume) and water (equal volume). Mixture dried by passing through a phase seperating cartridge. Solvent removed to give crude 1-bromo-4-(bromomethyl)-2-chlorobenzene (31.7 g, 94%) as pale brown oil which was progressed without further purification.

Workup

  1. temperatureat reflux for 18 hrs
  2. temperatureThe reaction was cooled
  3. washwashed with water (equal volume)
  4. customMixture dried
  5. customseperating cartridge
  6. customSolvent removed

Sources & evidence

ORD record
ord-d7b7ce96b3d146c3b4e18ba05e307d8a
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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