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Preparation method of trifluoroethyl-substituted aromatic compound

An aromatic compound, trifluoroethyl technology, applied in the field of preparation of trifluoroethyl-substituted aromatic compounds, can solve the problems of restricting industrial production safety, high risk of reaction reagents, high catalyst cost, etc., and achieve easy expansion of reaction scale, Low cost of raw materials and catalysts, good compatibility

Inactive Publication Date: 2017-05-31
SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method does not require the assistance of a transition metal catalytic system, the reaction involves 2,2,2-trifluorodiazoethane, a dangerous and explosive reaction intermediate, which greatly restricts the safety of industrial production.
[0004] It is not difficult to see that the above methods all have disadvantages such as high catalyst cost, large substrate limitation, and high risk of reaction reagents.

Method used

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  • Preparation method of trifluoroethyl-substituted aromatic compound
  • Preparation method of trifluoroethyl-substituted aromatic compound
  • Preparation method of trifluoroethyl-substituted aromatic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of compound 2,2,2-trifluoroethylbenzene

[0024]

[0025] Under a nitrogen atmosphere, phenylboronic acid (18.29g, 150mmol) and anhydrous sodium acetate (24.61g, 300mmol) were sequentially added to the sealed tube, and the solvent tetrahydrofuran (300mL) was added and stirred evenly, and then 2-iodo-1,1 , 1-trifluoroethane (20.99g, 100mmol), pyridine (1.58g, 20mmol) and Ni(cod) 2 (2.75g, 10mol), after sealing, stirred and reacted in an oil bath at 80°C for 12 hours, cooled the reaction solution to room temperature, added benzotrifluoride, and monitored the end point of the reaction using the fluorine spectrum internal standard method, and determined that the crude yield of the reaction was 32 % (the product 2,2,2-trifluoroethylbenzene has a low boiling point, and the yield was calculated without purification and separation).

Embodiment 2

[0027] Preparation of compound 2,2,2-trifluoroethylbenzene

[0028]

[0029] Under nitrogen atmosphere, phenylboronic acid (15.85g, 130mmol) and anhydrous potassium phosphate (74.29g, 350mmol) were successively added into the sealed tube, and the solvent dioxane (250mL) was added and stirred evenly, and then 2-iodo- 1,1,1-Trifluoroethane (20.99g, 100mmol), 2,2'-bipyridine (1.56g, 10mmol) and NiCl 2 (DME) (2.20g, 10mmol), after sealing, stirred and reacted in an oil bath at 80°C for 12 hours, cooled the reaction solution to room temperature, added benzotrifluoride, and monitored the end point of the reaction using the internal standard method of fluorine spectroscopy, and determined the crude product of the reaction. The rate is 60%.

Embodiment 3

[0031] Preparation of compound 2,2,2-trifluoroethylbenzene

[0032]

[0033] Under nitrogen atmosphere, add phenylboronic acid (15.85g, 130mmol) and anhydrous potassium phosphate (42.45g, 200mmol) in sequence in the sealed tube, add solvent toluene (200mL) and stir evenly, then add 2-iodo-1,1 , 1-trifluoroethane (20.99g, 100mmol), α,α,α-terpyridine (4.34g, 10mmol) and Ni(acac) 2 (2.57g, 10mmol), after sealing, stir and react in an oil bath at 80°C for 18 hours, cool the reaction solution to room temperature, add trifluorotoluene, use the fluorine spectrum internal standard method to monitor the reaction end point, and determine that the crude yield of the reaction is 38 %.

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Abstract

The invention belongs to the technical field of preparation of fluoroalkyl-substituted aromatic hydrocarbons, and in particular relates to a preparation method of a trifluoroethyl-substituted aromatic compound. The method takes a trifluoroethyl source reagent (I) and arylboronic acid Ar-B (OH) 2 (II) as raw materials, adopts a cheap and easily available nickel catalyst and pyridine ligands as a catalytic system, and efficiently introduces trifluoroethyl to an aromatic ring group, so that the trifluoroethyl-substituted aromatic compound can be obtained. According to the method, mild reaction conditions, high operability and low raw material cost are achieved, reaction scale is easy to expand, and product separation is simple, so the method has the advantages of being suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of fluoroalkyl-substituted aromatic hydrocarbons, in particular to a preparation method of trifluoroethyl-substituted aromatic hydrocarbon compounds. Background technique [0002] As the most electronegative element in the periodic table, fluorine has a strong electron-withdrawing ability and a small atomic volume, which can significantly regulate the physical, chemical and biological properties of organic molecules. It has been widely used in fields such as sexuality. At present, in pharmaceutical products and pesticide chemicals, fluorine-containing compounds account for about 20% and 30% respectively, and the proportion is also showing a gradually increasing trend. Among many fluorine-containing groups, the trifluoromethyl group with strong electron-withdrawing ability is favored by drug designers. Some trifluoromethyl-containing drugs are already on the market, such as Prozac for depress...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C22/08C07C17/263C07C41/30C07C43/225C07C253/30C07C255/50C07C67/343C07C69/76C07C45/68C07C47/55C07C49/80C07D213/64C07D215/12C07D319/18
CPCC07C17/263C07C41/30C07C45/68C07C67/343C07C253/30C07D213/64C07D215/12C07D319/18C07C22/08C07C43/225C07C255/50C07C69/76C07C47/55C07C49/80
Inventor 杨义刘晓强蔡俊杰蒋燕刘应乐郑玉彬
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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