Azobisisobutyronitrile → 1(3H)-Isobenzofuranone, 3-bromo-

HRID 485259Notes

Reaction equation

HRID 485259 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[O:2]1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH:1]1([Br:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[O:2]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 6885PhthalideHCID 67184N-bromobutanimide

Product 1

HCID 962181(3H)-Isobenzofuranone, 3-bromo-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1H-Isobenzofuran-3-one (40.2 g, 0.3 moles), N-bromosuccinimide (53.4 g., 0.03 moles) and azo-bisisobutyronitrile (1g) were combined in 500 mL of CCl4 and refluxed under nitrogen for 2 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate concentrated in vacuo to a solid residue. The latter was crystallized from cyclohexane to yield title product, 34.5 g., m.p. 78°-80° C.

Workup

  1. temperaturerefluxed under nitrogen for 2 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo to a solid residue
  4. customThe latter was crystallized from cyclohexane

Sources & evidence

ORD record
ord-94c8bc63d9594a6e86e79edf6d413015
Source dataset
uspto-grants-1985_08
Patent number
US04536393

Reaction notes

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