Toluene → 2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoline

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Reaction Steps

In a 100-mL three-neck flask, 0.46 g (1.7 mmol) of 2-chlorodibenzo[f,h]quinoline, 0.62 g (2.0 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 20 mL of toluene, 2 mL of ethanol, and 2 mL of a 2M aqueous solution of potassium carbonate were put. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 65 mg (56 μmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80° C. for 7 hours. After a predetermined time, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extract combined with the organic layer was washed with a saturated aqueous solution of sodium carbonate and a saturated solution of sodium chloride, and the resulting organic layer was dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene:hexane=1:1), so that a solid was obtained. The solid was purified by high performance liquid column chromatography. The high performance liquid column chromatography was performed using chloroform as a developing solvent. The obtained fraction was condensed to obtain a solid. A methanol suspension of the obtained solid was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that the objective substance was obtained as 0.68 g of white powder in 79% yield.

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