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Preparation method of deuterated chemical

A chemical, deuterated technology, applied in electrolytic components, electrolytic organic production, electrolytic process, etc., can solve the problem of low selectivity, achieve mild reaction conditions, controllable number, and reduce production costs

Active Publication Date: 2020-03-17
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a method for preparing deuterated chemicals, aiming at solving the problems that the existing deuterium addition reaction needs to use deuterium gas, high temperature, high pressure conditions, low selectivity, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Using deuterium water as a deuterium source, the electrocatalytic debromination and deuterium addition of 2-bromoacetophenone.

[0053]

[0054] Weigh 0.3mmol of 2-bromoacetophenone, 6mg of palladium acetylacetonate catalyst, 7.5mL of deuterium water, and 7.5mL of acetonitrile, respectively, and add them into a 30mL reaction bottle, replace the reaction system with argon protection state, and then place the graphite electrode in In the reaction bottle, set the voltage to 3.0V, turn off the power after 4 hours of reaction, and dilute the reaction mixture with 15mL CH 2 Cl 2 Extraction, the extract was dried with anhydrous sodium sulfate, the solvent was removed in vacuum, and the target product was separated by column chromatography. The high-resolution mass spectrum of the obtained product is shown in figure 1 , the resulting product was tested by GC-MS, HRMS, 1 HNMR, C-NMR, FT-IR and other tests confirmed that the yield of the reaction was 89%, and the...

Embodiment 2

[0055] Example 2: Using deuterium water as a deuterium source, the electrocatalytic debromination and deuterium addition reaction of 3-bromoacetophenone.

[0056]

[0057] Weigh 0.3mmol of 3-bromoacetophenone, 6mg of palladium acetylacetonate catalyst, 7.5mL of deuterium water, and 7.5mL of acetonitrile respectively, and add them into a 30mL reaction bottle, replace the reaction system with argon protection state, and then place the graphite electrode in In the reaction bottle, set the voltage to 3.0V, turn off the power after 4 hours of reaction, and dilute the reaction mixture with 15mL CH 2 Cl 2 Extraction, the extract was dried with anhydrous sodium sulfate, the solvent was removed in vacuum, and the target product was separated by column chromatography. The high-resolution mass spectrum of the obtained product is shown in figure 2 , the resulting product was tested by GC-MS, HRMS, 1 Tests such as HNMR, C-NMR, and FT-IR confirmed that the yield of the reaction was 8...

Embodiment 3

[0058] Example 3: Using deuterium water as a deuterium source, the electrocatalytic debromination and deuterium addition of 4-bromoacetophenone.

[0059]

[0060] Weigh 0.3mmol of 4-bromoacetophenone, 6mg of palladium acetylacetonate catalyst, 7.5mL of deuterium water, and 7.5mL of acetonitrile respectively, and add them into a 30mL reaction bottle, replace the reaction system with argon protection state, and then place the graphite electrode in In the reaction bottle, set the voltage to 2.6V, turn off the power after 4 hours of reaction, and dilute the reaction mixture with 15mL CH 2 Cl 2 Extraction, the extract was dried with anhydrous sodium sulfate, the solvent was removed in vacuum, and the target product was separated by column chromatography. The high-resolution mass spectrum of the obtained product is shown in image 3 , the resulting product was tested by GC-MS, HRMS,1 Tests such as HNMR, C-NMR, and FT-IR confirmed that the yield of the reaction was 88%, and the ...

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Abstract

The invention discloses a preparation method of a deuterated chemical. The method includes subjecting a halohydrocarbon compound and a deuterium source to dehalogenation and deuteration reactions under the co-catalysis of an electric field and a catalyst to obtain the deuterated chemical, wherein the deuterium source is one or more of deuterated water, a deuterated alcohol compound and a deuterated acid compound. The environmentally friendly and cheap deuterated water or deuteration agents are adopted as the deuterium source, in place of deuterium gas, and the fixed-point selective deuterationreaction of the halohydrocarbon is achieved under mild conditions under the function of electro-catalysis. Compared with the traditional deuteration reactions, the method has higher selectivity, milder reaction conditions, and more economic applicability, and is suitable for large-scale production of deuterated chemicals.

Description

technical field [0001] The invention relates to the field of electrocatalytic preparation of chemicals, in particular to a method for preparing deuterated chemicals. Background technique [0002] Deuterated chemicals are a special class of compounds that have important applications in the fields of reaction mechanism research, kinetics, drug metabolism, and biological structure determination. Heavy isotopes of hydrogen (deuterium or tritium) are usually introduced into the target compound through a multi-step synthesis. The currently commonly used hydrogen-deuterium exchange reaction is a very attractive strategy, but this method faces great challenges. On the one hand, hydrogen-deuterium exchange reactions often use deuterium gas as the source of deuterium, and most processes involve high temperature, high pressure, strong acid, and strong alkali conditions, so there are also high requirements for reaction equipment; on the other hand, the selectivity of hydrogen-deuterium...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 苏陈良张兵邱春天李瑛
Owner SHENZHEN UNIV
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