Synthetic Route of 24988-36-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 24988-36-1 as follows.
Into a 200-mL three-neck flask were put 7.1 g (24 mmol) of 1,5-dibromo-2,4-dimethoxybenzene, 2.8 g (20 mmol) of 2-fluorophenylboronic acid, 12 mL of toluene, 12 mL of diethylene glycol dimethyl ether, and 50 mL of a sodium carbonate aqueous solution (2 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 0.55 g (0.48 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at the same temperature for 3 hours. After the mixture was cooled down to the room temperature, 4.5 g (32 mmol) of 2-fluorophenylboronic acid and 0.12 g (0.29 mmol) of 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl were added to the mixture and then the mixture was degassed under reduced pressure. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. again. After that, 30 mg (0.13 mmol) of palladium(II) acetate was add ed to the mixture, and stirring was performed at the same temperature for 4 hours. After the stirring, the mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a brown oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was subjected to a gradient to change from hexane to chloroform gradually) to give 7.2 g (22 mmol) of a target pale yellow oily substance at a yield of 92%. A synthesis scheme of the above synthesis method is shown in (B-2) below.
According to the analysis of related databases, 24988-36-1, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Kawakami, Sachiko; Ishiguro, Yoshimi; Takahashi, Tatsuyoshi; Hamada, Takao; Seo, Hiromi; Seo, Satoshi; (113 pag.)US9997725; (2018); B2;,
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