N-bromobutanimide → 3,5-dibromoisobenzofuran-1(3H)-one

HRID 1091774Notes

Reaction equation

HRID 1091774 reaction equation
N(/C(C)(C)C#N)=N\C(C)(C)C#N.[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[O:18][CH2:17]2.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:24][CH:17]1[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([Br:13])[CH:15]=2)[C:19](=[O:23])[O:18]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178449904HCID 178449904, compound

Product 1

HCID 577917913,5-dibromoisobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-bromoisobenzofuran-1(3H)-one (E)-2,2′-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (0.540 g, 3.29 mmol) and 1-bromopyrrolidine-2,5-dione (5.85 g, 32.86 mmol) were dissolved CCl4 and heated at reflux for 2 hours. The reaction was cooled and filtered, the filtrate was evaporated to afford the desired material, as a yellow solid (6.05 g, 63.1% yield), which was used directly in the next stage.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-4312b64129c345d38aca1fa8d8795185
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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