Azobisisobutyronitrile → HCID 22616314, compound

HRID 842928Notes

Reaction equation

HRID 842928 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:11])[CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:4]1[CH:3]=[C:2]([Cl:1])[C:9]([Cl:10])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 226163174,5-Dichloro-2-methylbenzonitrile

Product 1

HCID 22616314HCID 22616314, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution 4,5-Dichloro-2-methyl-benzonitrile 7 (6.3 g, 33.9 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (9.0 g, 50.8 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield the tittle compound 4.0 g. (45%). 1H NMR (400 MHz, CDCl3) δ7.75 (s, 1 H, Ar), 7.66 (s, 1 H, Ar), 2.55 (s, 2 H, CH3).

Workup

  1. temperatureThe reaction mixture was refluxed 6 hrs
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompartitioned between ether and water
  5. dry with materialThe ether layer was dried
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (10% ether/hexanes)

Sources & evidence

ORD record
ord-e9128bd08ae34f129f59e4a6365b980b
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Reaction notes

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