Azobisisobutyronitrile → 6-bromomethyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19535

Reaction equation

HRID 19535 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([CH3:21])[CH:9]=2)=[O:5])[CH3:2].[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.[W]>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([CH2:21][Br:23])[CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 686992925-Methyl-3-oxo-1-phenylindene-2-carboxylic acid ethyl ester

Product 1

HCID 686975466-bromomethyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 36.7%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

6-Methyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (3 g, 10.3 mmol) obtained in Step 4 was dissolved in carbon tetrachloride, and N-bromosuccinimide (2 g, 11.4 mmol) and 2,2′-azobisisobutyronitrile (500 mg, 3.09 mmol) were added thereto. The mixture was refluxed for 3 hrs under the irradiation of a 375 W tungsten lamp. Upon the completion of the reaction, the resulting mixture washed with saturated saline and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 1.4 g of the titled compound (yield: 36.7%) in oil state.

Workup

  1. customUpon the completion of the reaction
  2. washthe resulting mixture washed with saturated saline
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-98d8b10c0bda4888ab506e69cf8a6076
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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