Azobisisobutyronitrile → 1-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19546

Reaction equation

HRID 19546 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][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]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClCCl.[W]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([Br:23])[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]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 118451126-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 686984701-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 74%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (1.5 g, 5.10 mmol) prepared in Preparation Example 1 was dissolved in dichloromethane (80 mL), and N-bromosuccinimide (1.09 g, 6.12 mmol) and 2,2′-azobisisobutyronitrile (0.08 mg, 0.51 mmol) were added thereto. The mixture was stirred for 2 hrs at RT under the irradiation of a 375 W tungsten lamp. Upon the completion of the reaction, the 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 (ethyl acetate/n-hexane=1/20→1/9) to obtain 1.4 g of the titled compound (yield: 74%) as a yellow solid.

Workup

  1. customUpon the completion of the reaction
  2. washthe 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 (ethyl acetate/n-hexane=1/20→1/9)

Sources & evidence

ORD record
ord-dbb54efd464f4ac8818e337f503f8cdb
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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