Synthesis method for 2,3,5,6-tetrafluorophenol

A synthesis method and technology of tetrafluorophenol are applied in the field of synthesis of 2,3,5,6-tetrafluorophenol, can solve the problems of unavailability, industrial production limitation, expensive pentafluorobenzene series compounds and the like, and achieve the reaction step The effect of short, good product purity and high reaction yield

Inactive Publication Date: 2015-09-23
ZHEJIANG ZHONGXIN FLUORIDE MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The industrial production of 2,3,5,6-tetrafluorophenol is greatly restricted due to the high price and low availability of pentafluorobenzene series compounds

Method used

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  • Synthesis method for 2,3,5,6-tetrafluorophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] To a 500ml dry reaction flask, replace the gas with nitrogen, add 22.5g of compound (I) and 90g of anhydrous ether, under the protection of nitrogen, stir and cool to -70~-80°C, slowly add 1.6M n-butyl Lithium-based n-hexane solution of 105 ml, after the dropwise addition was completed, the temperature was controlled at -60 to -70°C and the reaction was stirred for 2 hours. The temperature of the system was lowered to -70~-80°C, and 20.3 g of trimethyl borate was added dropwise. After the dropwise addition, the temperature was controlled at -60~-70°C to continue the reaction for 5 hours. Return the reaction system to room temperature, and slowly dilute it into 100 grams of 10% hydrochloric acid aqueous solution. After the dilution is complete, control the temperature at 20-30°C, add 21.9 grams of 35% hydrogen peroxide solution dropwise, and stir at 20-30°C. 30 hours. Add 60 grams of 10% sodium bisulfite solution to the reaction system, stir at room temperature for 1 ho...

Embodiment 2

[0032] In a 500ml dry reaction flask, replace the gas with nitrogen, add 15.0g of compound (I) and 180g of anhydrous toluene, under the protection of nitrogen, stir and cool to -60~-70°C, slowly add 1.5M n-propyl Lithium-based n-hexane solution of 87 ml, after the dropwise addition was completed, the temperature was controlled at -50 to -60°C and the reaction was stirred for 1 hour. Add 36.8 g of tri-n-butyl borate dropwise to the reaction system. After the dropwise addition, react at -50 to -60°C for 1 hour, then raise the temperature to -20 to -30°C to continue the reaction for 2 hours. Return the reaction system to room temperature, slowly dilute it into 100 g of 10% sulfuric acid aqueous solution, and recover toluene by distillation under reduced pressure after dilution, adjust the pH of the residual system to 4.0 with 10% sodium hydroxide solution, and add 15% hydrogen peroxide dropwise 45.3 g of aqueous solution, after the dropwise addition, the temperature of the system...

Embodiment 3

[0034]In a 500ml dry reaction flask, replace the gas with nitrogen, add 30.0g of compound (I) and 180g of anhydrous 2-tetrahydrofuran, under the protection of nitrogen, stir and cool to -70~-80°C, slowly add 2.5M 84 ml of n-hexane solution of n-butyllithium, after the dropwise addition was completed, the temperature was controlled at -60 to -70°C and the reaction was stirred for 1 hour. 41.4 g of tri-n-propyl borate was added dropwise. After the dropwise addition was completed, the temperature was controlled at -60 to -70°C and the reaction was stirred for 1 hour, and the temperature was raised to -30 to -40°C to continue the reaction for 3 hours. The reaction system was warmed to room temperature, and 100 grams of 12% sulfuric acid aqueous solution was added. After the addition, 32.6 grams of 25% hydrogen peroxide aqueous solution was added dropwise, and the system was heated to 30-40° C. and stirred for 20 hours. The reaction system was cooled down to room temperature, the o...

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Abstract

The invention discloses a synthesis method for 2,3,5,6-tetrafluorophenol, and belongs to the technical field of chemical synthesis. The synthesis method is characterized by comprising the following steps: (1) enabling reaction between 1,2,4,5-tetrafluorobenzene and an organic lithium agent in an inert solvent at low temperature to obtain an aryl lithium intermediate; enabling reaction between the obtained aryl lithium intermediate and boric acid ester at low temperature to obtain 2,3,5,6-tetrafluorobenzeneboronic acid and 2,3,5,6-tetrafluorobenzeneboronic acid ester through acid water quenching; (2) enabling reaction between the obtained 2,3,5,6-tetrafluorobenzeneboronic acid and 2,3,5,6-tetrafluorobenzeneboronic acid ester and hydrogen peroxide in an acidic aqueous system so as to obtain the 2,3,5,6-tetrafluorophenol. The synthesis method has the advantages that the raw materials are low in cost and easy to obtain, the synthesis steps are short, the reaction yield is high, and the product purity is good; the synthesis method is suitable for industrial application.

Description

Technical field: [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of 2,3,5,6-tetrafluorophenol. Background technique: [0002] 2,3,5,6-Tetrafluorophenol is an important fluorine-containing intermediate, which is widely used in drug synthesis and new material preparation. For example, using 2,3,5,6-tetrafluorophenol as a raw material, a peptide compound containing 2,3,5,6-tetrafluorophenoxy structure can be synthesized, which can be used to inhibit aspartate-specific cysteine Protease plays a role in the treatment of mediating cell apoptosis and various types of inflammation. Another example is to use 2,3,5,6-tetrafluorophenol as a raw material to synthesize the drug Robenicoxib for the treatment of arthritis, etc. [0003] At present, there are very few synthetic methods of 2,3,5,6-tetrafluorophenol that have been published, and only the synthetic route using pentafluorobenzene series compounds as raw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/27C07C37/01
CPCC07C37/01C07F5/025C07C39/27
Inventor 袁其亮俞伟樑钱捷施正军王超陈寅镐
Owner ZHEJIANG ZHONGXIN FLUORIDE MATERIALS CO LTD
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