Reaction #47824

Reaction equation

6-Methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

N-bromosuccinimide

2,2′-azobisisobutyronitrile

→

titled compound

Yield 74.0%

1-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic Acid Ethyl Ester

Yield 74.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherUpon the completion of the reaction
2. 2
   Washthe mixture washed with saturated saline
3. 3
   Extractionextracted with dichloromethane
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   Concentrationconcentrated under a reduced pressure
7. 7
   OtherThe resulting residue was purified by flash chromatography (ethyl acetate/n-hexane=1/20→1/9)

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.

Source