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

HRID 1709690Notes

Reaction equation

HRID 1709690 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-f975c6610df74bc09f0f214ed0cb421c
Source dataset
uspto-grants-1990_08
Patent number
US04950673

Reaction notes

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