Potassium Iodide → 1-(Bromomethyl)-3-chloro-5-methylbenzene

HRID 1709668Notes

Reaction equation

HRID 1709668 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O.[I-].[K+]>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:9])[CH:3]=1)[CH2:8][Br:10]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 328873,5-DimethylchlorobenzeneHCID 67184N-bromobutanimide

Product 1

HCID 123755491-(Bromomethyl)-3-chloro-5-methylbenzeneYield 109.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

A solution of 5-chloro-m-xylene (59.3 g) and dibenzoyl peroxide (5.0 g) in 1.13 L of benzene was heated at reflux. N-Bromosuccinimide (82.2 g) was added in portions over 15 minutes. Heating was continued for an additional 20 minutes until a negative potassium iodide reaction was observed. The reaction mixture was cooled, evaporated and then titurated with hexane (500 ml). The precipitated succinimide was removed by filtration and washed with additional hexane. Concentration afforded 101 g of crude 3-chloro-5-methylbenzyl bromide.

Workup

  1. temperatureat reflux
  2. temperatureHeating
  3. temperatureThe reaction mixture was cooled
  4. customevaporated
  5. customThe precipitated succinimide was removed by filtration
  6. washwashed with additional hexane
  7. concentrationConcentration

Sources & evidence

ORD record
ord-f2cc67aa63844ebea8751d54f0e84719
Source dataset
uspto-grants-1990_08
Patent number
US04950673

Reaction notes

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