Azobisisobutyronitrile → HCID 18521725, compound

HRID 467092Notes

Reaction equation

HRID 467092 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[O:11][C:12]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=2[CH:14]=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[O:11][C:12]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 131703102-Methyl-6-nitro-1-benzofuran

Product 1

HCID 18521725HCID 18521725, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide ("NBS") (1.11 g, 6.2 mmole) was added to a solution of 2-methyl-6-nitrobenzofuran (1.00 g, 5.65 mmole) and azobisisobutyronitrile (20 mg) in carbon tetrachloride and the mixture was heated at reflux temperature for 11/2 hours in the presence of a bright light. The solvent was then evaporated and the residue dissolved in methylene chloride, washed with water, dried (MgSO4), evaporated to dryness and purified by column chromatography on silica eluting with methylene chloride/hexane (7:3). The product-containing fractions were combined and evaporated to give the title compound, yield 1.43 g. 'H-N.m.r. clearly showed that the product contained 20% of 2-dibromomethyl-6-nitrobenzofuran, however, it was not considered necessary to remove this and the product was used directly without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 11/2 hours in the presence of a bright light
  3. customThe solvent was then evaporated
  4. dissolutionthe residue dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. custompurified by column chromatography on silica eluting with methylene chloride/hexane (7:3)
  9. customevaporated

Sources & evidence

ORD record
ord-df5f97d22f05436eab81e04e12a35fd8
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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