Potassium Carbonate → HCID 59537038, compound

Participants

Reaction Steps

In a 500 ml roundbottom flask were placed 17.6 g (61.1 mmol) 4,7-Dibromo-2-methyl-1H-indene, 26.3 g (2.5 eq.) 1-napthyl boronic acid, 274 mg (2 mol %) palladium acetate, 42.23 g (2.5 eq.) potassium carbonate, 39.4 g (2 eq.) tetrabutylammonium bromide, 169 ml degassed water and 169 ml degassed toluene. The mixture was stirred under reflux for 20 h. After cooling to room temperature, 100 ml toluene and 100 ml water were added. The aqueous phase was extracted 3 times with 100 ml toluene. The combined organic layers were washed once with 100 ml of 2M sodium hydroxide solution and 3 times with 50 ml water each, and dried over magnesium sulfate. Removal of the solvent in vacuo and purification via flash chromatography on silica using heptane/dichloromethane (10:1) yielded 15.3 g (40 mmol, 65%) of the desired indene as a white solid. 1H-NMR (500 MHz, CDCl3): δ=8.11, 7.89-7.77, 7.57-7.26 (3×m, 16H, aromatic), 6.61, 6.18 (2×s, 1H, indenyl-C═CH), 3.49 (“d”, 2H, benzylic), 2.09 (2×s, 3H, CH3) ppm.

Provenance & Evidence