Azobisisobutyronitrile → 2-Bromo-5-methoxy-3-phenyl-1H-inden-1-one

HRID 331389Notes

Reaction equation

HRID 331389 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]=[C:6]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][C:7]1[C:8](=[O:12])[C:9]2[C:5]([C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 703155925-Methoxy-3-phenyl-1H-inden-1-one

Product 1

HCID 104709362-Bromo-5-methoxy-3-phenyl-1H-inden-1-oneYield 66%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-Methoxy-3-phenyl-1H-inden-1-one (2.8 g, 11.85 mmol) obtained in Step 3 was placed into a flask and dissolved in CCl4 (20 mL). To the resulting solution, NBS (2.53 g, 14.22 mmol, 1.2 eq) and AIBN (280 mg, 10%/w) were added. The resulting mixture was allowed to reflux for 2 h. After cooling to room temperature, the reaction mixture was quenched with sat. Na2S2O3 (20 mL) extracted with CH2Cl2(20 mL×3). The organic layers were washed H2O and brine, dried over MgSO4 and concentrated in vacuo to give the desired product (2.45 g, 66%).

Workup

  1. temperatureto reflux for 2 h
  2. customthe reaction mixture was quenched with sat. Na2S2O3 (20 mL)
  3. extractionextracted with CH2Cl2(20 mL×3)
  4. washThe organic layers were washed H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b247d05e5a9b47a28051ae33b8319b6a
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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