Benzoyl Peroxide → HCID 14407249, compound

HRID 1194723Notes

Reaction equation

HRID 1194723 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:13])[CH:5]=[C:6]([C:8]([Cl:12])=[C:9]([Cl:11])[Cl:10])[CH:7]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:8]([Cl:12])=[C:9]([Cl:10])[Cl:11])[CH:7]=1)[CH2:13][Br:32]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14407248HCID 14407248, compound

Product 1

HCID 14407249HCID 14407249, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-chloro-5-(trichlorovinyl)toluene (7.56 g) and dibenzoyl peroxide (0.5 g) in 250 ml of benzene was heated at reflux. N-Bromosuccinimide (6.04 g) was added in portions and the reaction mixture stirred at reflux for 3 hours. The mixture was then evaporated and the residue titurated with hexane (200 ml). The precipitated succinimide was removed by filtration and washed with hexane (2 x 25 ml). The hexane was concentrated and the residual oil (10.1 g) chromatographed on silica with petroleum ether as eluant. The column afforded 1.39 g of starting toluene, 1.18 g of dibromide, and 6.57 g of the desired benzyl bromide.

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 3 hours
  3. customThe mixture was then evaporated
  4. customThe precipitated succinimide was removed by filtration
  5. washwashed with hexane (2 x 25 ml)
  6. concentrationThe hexane was concentrated
  7. customthe residual oil (10.1 g) chromatographed on silica with petroleum ether as eluant

Sources & evidence

ORD record
ord-071f49d823334f0d94d93accdc712715
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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