Azobisisobutyronitrile → HCID 22648021, compound

HRID 394080Notes

Reaction equation

HRID 394080 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:3]1[C:2]([Br:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=1[Br:11]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 70157802,6-DIBROMO-4-NITROTOLUENE

Product 1

HCID 22648021HCID 22648021, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,6-dibromo-4-nitrotoluene (3.83 g, 1 eq.), N-bromosuccinimide (3.23 g, 1.4 eq.) and dibenzoylperoxide (315 mg, 0.1 eq.) in CCl4 was degassed with argon. The mixture was brought to reflux and azobisisobutyronitrile (213 mg, 0.1 eq.) was added. The mixture was maintained at reflux for 6 hours. The reaction was cooled to room temperature, concentrated and purified to give 1-Bromomethyl-2,6-dibromo-4nitrobenzene. 1H NMR (500 MHz, CDCl3) δ CHCl3: 4.81 (2H, s), 8.41(2H, s).

Workup

  1. customwas degassed with argon
  2. temperatureto reflux
  3. temperatureThe mixture was maintained
  4. temperatureat reflux for 6 hours
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-79e4e911de75455abd1ee6a1793db1ff
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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