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With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 6.0h;Reflux;
Step 2: 2-Cyano-2',3'-dimethyl-biphenyl-4-olA mixture of <strong>[189680-06-6]4-bromo-3-cyanophenol</strong> (1.0 g, 5 mmol), 2,3-dimethylphenylboronic acid (1.1 g, 8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.43 mmol) and a 2M sodium carbonate solution (5 ml ) in 50 ml of 1 ,2-dimethoxyethane was heated at reflux for 6 hours. The mixture was cooled and was poured into an aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and filtered. The concentrated filtrate was purified by flash chromatography on silica gel using 0-10% ethyl acetate/heptane to provide the title compound, 133-7C, mp (0.33 g, 30%).
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 6.0h;Reflux;
Step 2: 2-Ethyl-2',3'-dimethyl-biphenyl-4-olA mixture of <strong>[99873-30-0]4-bromo-3-ethylphenol</strong> (1.6 g, 7.96 mmol), 2,3-dimethylphenylboronic acid (1.2 g, 7.96 mmol), tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.86 mmol) and a 2M sodium carbonate solution (6 ml) in 1 ,2-dimethoxyethane(70 ml) was heated at reflux for 6 hours. The mixture was cooled and was poured into an aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (150 ml). The organic layer was washed with water, dried over magnesium sulfate and filtered. The concentrated filtrate was purified by flash chromatography on silica gel using 100% heptane, then 9: 1 heptane:ethyl acetate to provide the title compound (0.7 g, 39%).
With dichlorobis(triphenylphosphine)palladium[II]; In 1,2-dimethoxyethane;
(1) Synthesis of 4-(2,3-dimethylphenyl)indene 38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (66.7 mmol) of 2,3-dimethylphenylboronic acid, 10.8 g (55.4 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 1.0 g (1.42 mmol) of dichlorobis(triphenylphosphine)palladium, and 1.30 g (4.96 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 11 hours. This was left cooled to room temperature, and the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. 6 mL of concentrated hydrochloric acid was added to the hexane solution at room temperature, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered away through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and then dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 11.66 g (yield 96%) of 4-(2,3-dimethylphenyl)indene as a colorless oil.
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 90℃; for 11h;
38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (66.7 mmol) of 2,3-dimethylphenylboronic acid, 10.8 g (55.4 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 1.0 g (1.42 mmol) of dichlorobis(triphenylphosphine)palladium, and 1.30 g (4.96 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 11 hours. This was left cooled to room temperature, and the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. 6 mL of concentrated hydrochloric acid was added to the hexane solution at room temperature, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered away through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and then dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 11.66 g (yield 96%) of 4-(2,3-dimethylphenyl)indene as a colorless oil.
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