Potassium Iodide → 3-Methyl-5-(trifluoromethyl)benzyl bromide

HRID 1194744Notes

Reaction equation

HRID 1194744 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH3:10])[CH:6]=[C:7]([CH3:9])[CH:8]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:31]N1C(=O)CCC1=O.[I-].[K+]>C1C=CC=CC=1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[CH2:10][Br:31]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 204346091,3-Dimethyl-5-(trifluoromethyl)benzene

Product 1

HCID 27756233-Methyl-5-(trifluoromethyl)benzyl bromide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5-trifluoromethyl-m-xylene (3.4 g) and dibenzoyl peroxide (0.25 g) in 100 ml of benzene at reflux is treated with N-bromosuccinimide (4.4 g) in portions. The mixture is heated until a negative potassium iodide test is obtained. The reaction mixture is cooled and concentrated in vacuo. The residue is triturated with n-hexane and the solids are removed by filtration. The filtrate is evaporated to give the oily crude benzyl bromide.

Workup

  1. customis obtained
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue is triturated with n-hexane
  5. customthe solids are removed by filtration
  6. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-24479168aa5c4be7b4c607b33aa822aa
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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