反应详情

phenylboronic acid (8.3 g, 68 mmol) was dissolved in ethylene glycol dimethylether (DME, 100 mL), and aqueous solution (100 mL) of cesium carbonate (30 g), 4-bromo-5-methylindene (10 g, 48 mmol), tetrakis(triphenylphosphine)palladium (3.0 g, 2.6 mmol) were sequentially added. Solution was reacted for 55 hours while heating under reflux, then, reaction solution was added into water (200 mL), and extracted with diisopropylether. Organic layer was washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride, then was dried over sodium sulfate, and solvent was distilled off under reduced pressure to obtain the crude product. This was purified by silica-gel column chromatography (Silica-gel 60: produced by Kanto Chemical Co., Inc, hexane) to obtain 4-phenyl-5-methylindene (8.5 g, yield: 86%) as colorless liquid.

1. customSolution was reacted for 55 hours
2. temperaturewhile heating
3. temperatureunder reflux
4. customreaction solution
5. extractionextracted with diisopropylether
6. washOrganic layer was washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride
7. dry with materialwas dried over sodium sulfate, and solvent
8. distillationwas distilled off under reduced pressure
9. customto obtain the crude product
10. customThis was purified by silica-gel column chromatography (Silica-gel 60: produced by Kanto Chemical Co., Inc, hexane)