Potassium Iodide → HCID 23036227, compound

HRID 1194738Notes

Reaction equation

HRID 1194738 reaction equation
[F: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.[I-].[K+]>C1C=CC=CC=1>[F: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

6

Reactant 4

HCID 4875Potassium IodideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 23036217HCID 23036217, compound

Product 1

HCID 23036227HCID 23036227, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-fluoro-5-(trichlorovinyl)toluene (2.39 g) and dibenzoyl peroxide (0.2 g) in 60 ml of benzene at reflux, N-bromosuccinimide (2.21 g) is added in portions. The mixture is heated at reflux until the solution gives a negative reaction with potassium iodide. The reaction mixture is concentrated and the residue triturated with 100 ml of hexane. The precipitated succinimide is collected by filtration and the filtrate concentrated and then chromatographed on silica gel (hexane) to give the desired benzyl bromide.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux until the solution
  3. customgives
  4. concentrationThe reaction mixture is concentrated
  5. customthe residue triturated with 100 ml of hexane
  6. filtrationThe precipitated succinimide is collected by filtration
  7. concentrationthe filtrate concentrated
  8. customchromatographed on silica gel (hexane)

Sources & evidence

ORD record
ord-fb80bc6f63434dcfb03c247bf33b140b
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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