Benzoyl Peroxide → 4-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

HRID 216707Notes

Reaction equation

HRID 216707 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:13])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27756354-Methyl-3-(trifluoromethyl)bromobenzene

Product 1

HCID 534180314-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Bromo-1-methyl-2-trifluoromethyl-benzene (3 g, 12.55 mmol), N-bromosuccinimide (2.68 g, 15.06 mmol, 1.2 eq) and dibenzoylperoxid (60 mg, 2.5 mmol, 0.02 eq) are stirred in carbon tetrachloride under ultraviolet light at reflux for 5 h. The reaction mixture is cooled to RT, filtered and the filtrate is concentrated in vacuo. The residue is carefully purified by chromatography (silicagel, pure hexanes) to afford the title compound as a colorless liquid.

Workup

  1. temperatureat reflux for 5 h
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residue is carefully purified by chromatography (silicagel, pure hexanes)

Sources & evidence

ORD record
ord-88b928d7bc08411589c265e5fbf2bde4
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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