Azobisisobutyronitrile → HCID 18521725, compound

HRID 1761880Notes

Reaction equation

HRID 1761880 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.

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-bef1bd937ce94d91971841cbb75bbdc7
Source dataset
uspto-grants-1989_05
Patent number
US04829071

Reaction notes

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