Potassium Carbonate → 9-Phenyl-9H,9'H-[3,3']bicarbazolyl

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Reaction Steps

Into a 200 mL three-neck flask were put 2.5 g (10 mmol) of 3-bromocarbazole, 2.9 g (10 mmol) of N-phenylcarbazole-3-boronate, and 152 mg (0.50 mmol) of tri(o-tolyl)phosphine. The air in the flask was replaced with nitrogen. To the mixture were added 50 mL of dimethoxyethanol (DME) and 10 mL of potassium carbonate solution (2 mol/L). Under reduced pressure, this mixture was degassed while being stirred. After the degassing, 50 mg (0.2 mmol) of palladium acetate was added to the mixture. This mixture was stirred at 80° C. for 3 hours under a stream of nitrogen. After the stirring, about 50 mL of toluene was added to this mixture. The mixture was stirred for about 30 minutes and then washed with water and a saturated aqueous sodium chloride solution in that order. After the washing, the organic layer was dried with magnesium sulfate. This mixture was subjected to gravity filtration. The obtained filtrate was condensed to give an oily substance. The obtained oily substance was dissolved in toluene. This solution was subjected to filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The obtained filtrate was condensed to give 3.3 g of a white solid, which was the object of the synthesis, in a yield of 80%. A synthesis scheme of Step 1 is shown in (b-1) given below.

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