Azobisisobutyronitrile → HCID 12668053, compound

HRID 842925Notes

Reaction equation

HRID 842925 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[Br:11]NC(=O)CCC(N)=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10][Br:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 1427424-Chloro-2-methylbenzonitrileHCID 9834204N-Bromosuccinamide

Product 1

HCID 12668053HCID 12668053, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution 4-Chloro-2-methyl-benzonitrile 1(5.0 g, 33.0 mmol) in carbon tetrachloride (150 mL) was added N-bromosuccinamide (7.6 g, 42.9 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 a white solid (40%). 1H NMR (400 MHz, CDCl3) δ7.61 (d, J=8.3 Hz, 1 H, Ar), 7.57 (d, J=2.2 Hz, 1 H, Ar), 7.41 (dd, J=8.3, 2.0 Hz, 1 H, Ar), 4.59 (s, 2 H, CH2).

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-51aa161f49f245d7895c5ba0226e0e5d
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Reaction notes

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