Azobisisobutyronitrile → 2-Bromo-1-oxo-3-phenyl-1H-inden-6-yl acetate

HRID 331262Notes

Reaction equation

HRID 331262 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][C:11]2=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1C(=O)N([Br:28])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:10]([Br:28])[C:11]2=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 703172342,3-Dihydro-1-oxo-3-phenyl-1H-inden-6-yl acetate

Product 1

HCID 703132412-Bromo-1-oxo-3-phenyl-1H-inden-6-yl acetateYield 92.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2,3-Dihydro-1-oxo-3-phenyl-1H-inden-6-yl acetate (10.1 g, 37.9 mmol) obtained in Step 3 was placed into a flask and dissolved in CCl4 (200 mL). To the resulting solution, NBS (14.8 g, 2.2 eq) and AIBN (0.62 g, 10 mol %) were added. The resulting mixture was allowed to reflux for 1 h. Then the mixture was further irradiated by a tungsten lamp (375W) for 1.5 h. After cooling to room temperature, the precipitate was collected using a Buchner funnel. The solid was dissolved in CH2Cl2 and washed with sat. Na2S2O3, H2O, and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give the desired product (12.0 g, 92%).

Workup

  1. temperatureto reflux for 1 h
  2. customthe precipitate was collected
  3. dissolutionThe solid was dissolved in CH2Cl2
  4. washwashed with sat. Na2S2O3, H2O, and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dad5f08ce8fb4ba78967408f6e963a70
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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