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Preparation method of deuterated benzene compound

A compound, deuterated benzene technology, applied in the field of deuterated compound synthesis, can solve problems such as substrate versatility limitation, and achieve the effects of simple and efficient synthesis method, simple and convenient operation process, and easy to obtain.

Pending Publication Date: 2022-01-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis of deuterated arene derivatives has been extensively developed, the direct H–D exchange reaction of arenes still suffers from the limitation of substrate versatility.

Method used

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  • Preparation method of deuterated benzene compound
  • Preparation method of deuterated benzene compound
  • Preparation method of deuterated benzene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The generation of embodiment 1 deuterated toluene

[0027]

[0028] Add 0.25mmol (23.035mg) of toluene, 2mL of deuterium water, 24.38mg of 10% platinum carbon, 0.1mL of isopropanol and 0.9mL of cyclohexane solution into a 50mL three-necked flask equipped with a condenser, a thermometer and electromagnetic stirring, and use nitrogen gas Replace the air in the reaction system, then raise the temperature to 70°C, react at this temperature for 12 hours, then lower to room temperature, remove the catalyst platinum carbon by filtration, and obtain a mixture of deuterium water and crude product. 10 mL of dichloromethane was added to the mixture, the organic layer and the deuterium water layer were separated, the lower organic layer liquid was collected, and the organic layer liquid was rotary evaporated at 38° C. to obtain 17.184 mg of the product deuterated toluene liquid, with a yield of 74.6%. The MS spectrum of deuterated toluene is as follows figure 1 As shown, the NM...

Embodiment 2

[0030] Add 0.25mmol (23.035mg) of toluene, 2mL of deuterium water, 24.38mg of 10% palladium carbon, and 1mL of isopropanol solution into a 50mL three-necked flask equipped with a condenser, a thermometer and electromagnetic stirring, and replace the air in the reaction system with nitrogen , and then heated up to 70 ° C, reacted at this temperature for 12 hours and then lowered to room temperature, and the catalyst palladium carbon was removed by filtration to obtain a mixture of deuterium water and crude product. 10 mL of dichloromethane was added to the mixture, the organic layer and the deuterium water layer were separated, the lower organic layer liquid was collected, and the organic layer liquid was rotary evaporated at 38° C. to obtain 16.17 mg of the product deuterated toluene liquid, with a yield of 70.2%.

Embodiment 3

[0032] Add 0.25mmol (23.035mg) of toluene, 2mL of deuterium water, 24.38mg of 10% platinum carbon and 1mL of isopropanol in a 50mL three-necked flask equipped with a condenser tube, a thermometer and electromagnetic stirring, and replace the air in the reaction system with nitrogen, Then the temperature was raised to 70° C., reacted at this temperature for 12 hours, and then cooled to room temperature, and the catalyst platinum carbon was removed by filtration to obtain a mixture of deuterium water and crude product. 10 mL of dichloromethane was added to the mixture, the organic layer and the deuterium water layer were separated, the lower organic layer liquid was collected, and the organic layer liquid was rotary evaporated at 38° C. to obtain 16.1245 mg of the product deuterated toluene liquid, with a yield of 70%.

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Abstract

The invention relates to the field of organic chemistry, and discloses a preparation method of a deuterated benzene compound, in the method, active carbon supported noble metal is mainly used as a catalyst, deuterium water is used as a deuterium source, and the deuterated benzene compound is prepared from a benzene compound. Wherein in a reaction system, isopropanol is activated on the surface of a catalyst, trace active hydrogen is generated in situ, oxidative addition and reduction elimination reactions are carried out, and finally deuterium atoms in deuterium water and hydrogen atoms in a benzene ring compound are exchanged to generate the deuterated benzene compound. Compared with a traditional deuteration reaction, the method has the following advantages that conditions are mild, reaction raw materials are easy to obtain, and the deuteration reaction of benzene substances can be completed under the hydrogen-free condition; and in the reaction process, deuterium gas is prevented from being used as a deuterium source, so that the occurrence of excessive deuterium addition reaction and the safety problem are avoided, and the producing cost is reduced. And the reaction product is clean and has high yield.

Description

technical field [0001] The invention relates to the technical field of deuterated compound synthesis, and mainly relates to a preparation method of deuterated benzene compounds. Background technique [0002] Deuterium is a hydrogen isotope consisting of a proton and a neutron. Due to the mass effect, carbon-deuterium bonds have shorter bond lengths and higher bond energies than carbon-hydrogen bonds. Therefore, deuterated compounds are widely used in fields such as medicine, environmental analysis and detection, and development of new materials. In the field of medicine, by replacing one or more carbon-hydrogen bonds (C-H) in specific metabolic sites of drug molecules with carbon-deuterium bonds (C-D), the drug metabolism cycle can be extended and the generation of toxic metabolites can be reduced, thereby reducing the dosage, Improve safety and obtain better efficacy. In 2017, the world's first deuterated drug, AUSTEDO (deuterated tetrabenazine), was approved by the U.S....

Claims

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Application Information

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IPC IPC(8): C07B59/00C07C5/00C07C7/10C07C15/06C07C37/00C07C37/72C07C39/04C07C51/347C07C51/48C07C63/06C07C17/35C07C17/38C07C25/06C07C25/02C07C209/68C07C209/84C07C211/46C07C15/14C07C45/61C07C45/80C07C49/78C07C49/786
CPCC07B59/001C07C5/00C07C7/10C07C37/001C07C37/72C07C51/347C07C51/48C07C17/35C07C17/38C07C209/68C07C209/84C07C45/61C07C45/80C07B2200/05C07C2523/42C07C15/06C07C39/04C07C63/06C07C25/06C07C25/02C07C211/46C07C15/14C07C49/78C07C49/786Y02P20/52
Inventor 王建国江文杰邵方君王潇剑马帆冬程家旭
Owner ZHEJIANG UNIV OF TECH
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