Benzoyl Peroxide → HCID 23036221, compound

HRID 1194732Notes

Reaction equation

HRID 1194732 reaction equation
[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([CH3:13])[CH:9]=[C:10]([CH3:12])[CH:11]=1)=[C:3]([Cl:5])[Cl:4].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>C1C=CC=CC=1>[CH3:13][C:8]1[CH:9]=[C:10]([CH:11]=[C:6]([C:2]([Cl:1])=[C:3]([Cl:5])[Cl:4])[CH:7]=1)[CH2:12][Br:32]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 23036245HCID 23036245, compound

Product 1

HCID 23036221HCID 23036221, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a refluxing solution of 5-(trichlorovinyl)-m-xylene (32.28 g) and dibenzoyl peroxide (3.43 g) in 1300 ml of benzene, N-bromosuccinimide (30.21 g) was added in portions. The resulting mixture was heated at reflux for 30 minutes at which point no N-bromosuccinimide was evident. The reaction mixture was concentrated under reduced pressure and the residue triturated with 250 ml of hexane. The precipitated succinimide was collected by filtration and thoroughly washed with hexane. The filtrate was concentrated and the residue chromatographed on silica (petroleum ether) to give 26.2 g of the desired benzyl bromide.

Workup

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue triturated with 250 ml of hexane
  4. filtrationThe precipitated succinimide was collected by filtration
  5. washthoroughly washed with hexane
  6. concentrationThe filtrate was concentrated
  7. customthe residue chromatographed on silica (petroleum ether)

Sources & evidence

ORD record
ord-2c0ade1583f24e5194be3eac64cca2e3
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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