1,2,4-Trimethylbenzene → HCID 59523758, compound

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Reaction Steps

Under the nitrogen atmosphere, 4-(anthracen-9-yl)naphthalen-1-yl trifluoromethane sulfonate (30.0 g) as the sixteenth intermediate compound, phenylboronic acid (12.1 g), Pd(PPh3)4 (2.3 g), potassium phosphate (28.1 g), and a mixture solvent of pseudo cumene, t-butyl alcohol, and water (150 ml) (pseudo cumene/t-butyl alcohol/water=8/1/1 (volume ratio)) were added to a flask and refluxed for 5.5 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with water to terminate the reaction. It was then extracted with toluene. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (solvent: heptane/toluene mixture solvent). At that time, with reference to the method described in “Guideline for Experiments of Organic Chemistry (1)—Method of handling substance and separation and purification method”—published by Kagaku-Dojin Publishing Company, INC., page 94, the target compound was eluted by gradually increasing the ratio of toluene in the eluent. The crude product obtained by removing the solvent by distillation under reduced pressure was washed with heptane, followed with methanol to give 9-(4-phenylnaphthalen-1-yl)anthracene (24.1 g) as a seventeenth intermediate compound. The scheme is shown in the following “Reaction 28”.

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