反应详情

4-(4-methoxyphenoxy)-5-methyl-7-nitroindane (197 mg) and 4-fluorobenzoyl chloride (194 μL) were dissolved in dichloromethane (3.9 mL). Titanium tetrachloride (360 μL) was added dropwise to the solution under ice-cooling with stirring. The mixture was stirred under an argon atmosphere at room temperature for 15 hours. Adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=9/1) to give (4-fluorophenyl)-[2-methoxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanone (155 mg).

1. temperaturecooling
2. stirringThe mixture was stirred under an argon atmosphere at room temperature for 15 hours
3. extractionAdding water, the reaction mixture was extracted with ethyl acetate
4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water and brine successively
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed under reduced pressure
7. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=9/1)