Azobisisobutyronitrile → 2-Bromoindenone

HRID 331252Notes

Reaction equation

HRID 331252 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:18][C:2]1[C:1](=[O:10])[C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67351-IndanoneHCID 67184N-bromobutanimide

Product 1

HCID 99906492-Bromoindenone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The indanone compound of formula 6 prepared in Step 3, NBS (2 to 3 eq), and AIBN (1 to 0.2 eq) are dissolved in CCl4. Then, the mixture is allowed to reflux for 30 min to 1 h with stirring and then is further irradiated by a tungsten lamp (375 W) for 1 to 2 h with stirring, to obtain the 2-bromo-1H-indenone of formula 7. In other way, the mixture may be allowed to reflux for 2 to 9 h with stirring while being irradiated by a tungsten lamp (375 W), to obtain the 2-bromo-1H-indenone of formula 7.

Workup

  1. temperatureto reflux for 30 min to 1 h
  2. customis further irradiated by a tungsten lamp (375 W) for 1 to 2 h
  3. stirringwith stirring

Sources & evidence

ORD record
ord-06f01594d913490e8c64c4147c6cb722
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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