N-bromobutanimide → HCID 23036236, compound

HRID 1194725Notes

Reaction equation

HRID 1194725 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([Cl:13])=[C:10]([Cl:12])[Cl:11].[Br:14]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:14])=[CH:4][C:3]=1[C:9]([Cl:13])=[C:10]([Cl:11])[Cl:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14033037HCID 14033037, compound

Product 1

HCID 23036236HCID 23036236, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

A solution of 4-chloro-3-(trichlorovinyl)toluene (13.77 g) and dibenzoyl peroxide (1.0 g) in 500 ml of benzene was heated at reflux. N-Bromosuccinimide (11.6 g) was added in portions and the resulting mixture stirred at reflux for 1.5 hours (negative KI test). The reaction mixture was concentrated under reduced pressure. The residue was partially dissolved in 300 ml of petroleum ether and the insoluble succinimide removed by filtration. The filtrate was concentrated to give 17.9 g of the benzyl bromide.

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 1.5 hours (negative KI test)
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe residue was partially dissolved in 300 ml of petroleum ether
  5. customthe insoluble succinimide removed by filtration
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c9fe6ed069ce47d2b16f780e914ee1d9
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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