Azobisisobutyronitrile → 1-Bromo-2-bromomethyl-4-methoxy-5-trifluoromethyl-benzene

HRID 604173Notes

Reaction equation

HRID 604173 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[CH3:14].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[CH2:14][Br:27]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 66602689Benzene, 1-bromo-4-methoxy-2-methyl-5-(trifluoromethyl)-

Product 1

HCID 666026811-Bromo-2-bromomethyl-4-methoxy-5-trifluoromethyl-benzeneYield 56.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-Bromo-4-methoxy-2-methyl-5-trifluoromethyl-benzene (1.0 g), 2,2′-azobisisobutyronitrile (61 mg) and N-bromosuccinimide (795 mg) are dissolved in carbon tetrachloride (15 ml) and the mixture is heated under reflux overnight. The reaction solution is cooled to room temperature and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1) to give 1-bromo-2-bromomethyl-4-methoxy-5-trifluoromethyl-benzene (732 mg).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1)

Sources & evidence

ORD record
ord-f1b129f991ae467882171b2908f2b386
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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