Method for synthesizing substituted biphenyl compound
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A synthesis method and compound technology are applied in the synthesis field of biphenyl compounds, which can solve the problems of complicated operation and high cost of the preparation method, and achieve the effects of low price, reduced material cost and enlarged production.
Active Publication Date: 2018-07-06
SUZHOU KELUN PHARMA RES CO LTD +1
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[0008] The technical problem to be solved by the present invention
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[0041] Example 1
[0042] A 1000mL three-necked flask was sequentially added 4-(methylsulfonyl)phenylboronic acid (10.0g, 50mmol), 4'-bromo-2,2,2-trifluoroacetophenone (12.5g, 50mmol), 10% palladium on carbon ( 0.5g), sodium carbonate (15.0g, 150mmol), 100mL each of methanol and water, the reaction flask was evacuated and filled with nitrogen, and reacted at 30°C for 8 hours. TLC showed that all the raw materials had reacted. Stop the reaction. Add 200mL ethyl acetate to the reaction flask. After stirring for 1 h, suction filtration, the upper ethyl acetate phase was separated, and the solvent was removed to obtain 15.2 g of white solid with a yield of 92.6%.
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[0043] Example 2
[0044] A 1000mL three-necked flask was sequentially added 4-(methylsulfonyl)phenylboronic acid (10.0g, 50mmol), 4'-bromo-2,2,2-trifluoroacetophenone (12.5g, 50mmol), 10% palladium on carbon ( 0.5g), sodium carbonate (15.0g, 150mmol), 100mL of ethanol and water each, the reaction flask was evacuated and filled with nitrogen, and reacted at 30°C for 8 hours. TLC showed that all the raw materials had reacted. Stop the reaction. Add 200mL ethyl acetate to the reaction flask. After stirring for 1 h, suction filtration, the upper ethyl acetate phase was separated, and the solvent was removed to obtain 14.6 g of white solid with a yield of 89.0%.
Example Embodiment
[0045] Example 3
[0046] A 1000mL three-necked flask was sequentially added 4-(methylsulfonyl)phenylboronic acid pinacol ester (14.1g, 50mmol), 4'-bromo-2,2,2-trifluoroacetophenone (12.5g, 50mmol), 10 % Palladium on carbon (0.5g), sodium carbonate (15.0g, 150mmol), methanol and water 100mL, the reaction flask was evacuated and filled with nitrogen, and reacted at 30°C for 8 hours. TLC showed that all the raw materials had reacted. Stop the reaction. Add 200mL to the reaction flask Ethyl acetate was stirred for 1 h, filtered with suction, the upper ethyl acetate phase was separated, and the solvent was removed to obtain 14.2 g of white solid, with a yield of 86.5%.
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Abstract
The invention belongs to the field of organic synthesis, and relates to a method for synthesizing a substituted biphenyl compound. Technical problems to be solved in the invention are tedious operation and high cost of existing preparation methods. The method for synthesizing the substituted biphenyl compound having structural formula I, provided to solve the technical problems, comprises the following steps: a compound of formula II reacts with a compound of formula III in a mixed solvent in the presence of an alkali under the catalysis of palladium on carbon under the protection of an inertgas; and a reaction solution obtained after the reaction ends is filtered, the obtained filtrate is extracted with an extractant, and the obtained extract is concentrated to obtain the biphenyl compound represented by formula (I). The method for synthesizing the substituted biphenyl compound has the advantages of simplification of the post-treatment process, simplification of the product refiningand purifying process, and realization of great reduction of the energy consumption in the reaction and facilitation of industrial production due to the reaction being effectively performed at room temperature. The structure of the substituted biphenyl compound is represented by the formula I shown in the description; and the structures of the formula II and the formula III are also shown in the description.
Description
technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of biphenyl compounds. Background technique [0002] The construction of Aryl-aryl bonds is an important method in modern organic synthesis, and many natural products (such as alkaloids) and biologically active drug molecules contain biaryl ring structural units. As one of the effective ways to synthesize Aryl-aryl bonds, the Suzuki coupling reaction is mainly characterized by the use of metal catalysts to catalyze the coupling reaction of carbon-carbon bonds between organoboron compounds and halogen compounds in high-boiling polar solvents. Reaction of Arylboron Compounds and Arylhalogen Compounds. Metal catalysts are usually Pd metal or Ni metal catalysts, and solvents are commonly used DMSO, DMF, DME, DMA, dioxane, etc. In the reaction, the metal catalyst is usually used in coordination with the complex, which can be tetrakistriphenylphosphine,...
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