Azobisisobutyronitrile → HCID 68760715, compound

HRID 1026247Notes

Reaction equation

HRID 1026247 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[CH3:2].[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(OCC)(=O)C>[Br:14][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 3503664-ethoxy-1-methyl-2-nitrobenzene

Product 1

HCID 68760715HCID 68760715, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-ethoxy-1-methyl-2-nitrobenzene (11.8 g), N-bromosuccinimide (17.4 g), 2,2′-azobisisobutyronitrile (1.07 g) and ethyl acetate (300 mL) was stirred under an argon atmosphere at 90° C. overnight. The solvent was evaporated under reduced pressure, and the residue was diluted with diethyl ether, and the mixture was washed three times with water. The separated organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a yellow oil (11.3 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with diethyl ether
  3. washthe mixture was washed three times with water
  4. washThe separated organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-87cfd163d8c74113a7222244c48f9e8a
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…