Water → 4-Phenyl-5-methylindene

Participants

Reaction Steps

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.

Provenance & Evidence