Azobisisobutyronitrile → 3-bromoindenone

HRID 331257Notes

Reaction equation

HRID 331257 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[CH:3][CH:4]=2)[C:8](=[O:12])[CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 787875-Methoxyindan-1-one

Product 1

HCID 113562513-bromoindenone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-methoxyindanone of formula 20 is dissolved in CCl4, N-bromosuccinimide (2 to 2.2 eq) and 2,2′-azobisisobutyronitrile (0.2 to 0.3 eq) are added thereto. The resulting mixture is further irradiated by a tungsten lamp (375W) for 3 to 5 h with stirring, to obtain the 3-bromoindenone of formula 21.

Sources & evidence

ORD record
ord-f1ad0a4bfd5046a8a03c0a93ced7a273
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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