Cesium carbonate → 2,5-Dimethyl-4-(3,5-dimethylphenyl)indene

Participants

Reaction Conditions

Reaction Steps

3,5-Dimethylphenylboronic acid (2.3 g, 15 mmol), prepared as described under (e) above, cesium carbonate (4.9 g, 15 mmol), and Pd2(dba)3 (87 mg, 94 μmol) (dba=dibenzylidene acetone) were dissolved in 30 ml of 1,4-dioxane. To the resultant solution were added P(t-Bu)3 (57 μL, 280 μmol) and 4-bromo-2,5-dimethylindene (3.1 g, 15 mmol) and the reaction was stirred at 80° C. for five hours. After this time, the solvent was removed in vacuo and the residue was taken up in 100 ml of diethyl ether and filtered through a celite-packed frit to remove cesium salts. Thereafter the solvent was removed in vacuo and the residue was loaded onto a silica gel column and eluted with hexane. Yield: 2.1 g (56%).

Provenance & Evidence