Azobisisobutyronitrile → HCID 67119147, compound

HRID 2076576Notes

Reaction equation

HRID 2076576 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH3:21][C:22]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:23]=1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C1C=CC=CC=1>[Br:1][CH2:21][C:22]1[CH:34]=[CH:33][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:31][C:23]=1[C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 671192671,1-Dimethylethyl 2-methyl-5-(trifluoromethyl)benzoate

Product 1

HCID 67119147HCID 67119147, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-Bromosuccinimide (1.18 g, 6.63 mmol) and 2,2′-azobis(isobutyronitrile) (20 mg) were added to a solution of tert-butyl 2-methyl-5-(trifluoromethyl)benzoate (1.57 g, 6.03 mmol) obtained in Example (2-1) in benzene (25 ml) and the mixture was heated under reflux for 60 minutes. The temperature of the reaction mixture was returned to room temperature and the residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=8/1-6/1) to give tert-butyl 2-(bromomethyl)-5-(trifluoromethyl)benzoate as a white powder (1.08, yield: 53%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 60 minutes
  3. customwas returned to room temperature
  4. customthe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=8/1-6/1)

Sources & evidence

ORD record
ord-35b3eb8aae5c47ceabb34c0cdd50cd56
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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