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Preparation method of benzene-d6

A technology of -d6 and hexahalogenated benzene, which is applied in the field of preparation of benzene-d6, can solve the problems of unfavorable large-scale production, impurities in products, high price, etc., and achieve the goal of breaking the dependence on imports, shortening the production cycle and reducing the dosage Effect

Active Publication Date: 2020-08-28
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a high isotope utilization rate, but the product contains impurities and is difficult to purify, which is not conducive to large-scale production
At present, the source of benzene-d6 in China mainly depends on imports, which has the disadvantage of being expensive. Therefore, it is necessary to develop a method for preparing benzene-d6 with high isotope utilization rate, high product purity and easy operation.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Slowly add 14.2g of hexachlorobenzene into 1200g of anhydrous ether in a dry room temperature environment, and stir at a rate of 200rpm. After stirring for 0.5 hours, a clear solution A is obtained; the clear solution A is transferred to an autoclave with a volume of 3000mL 8.4g of lithium aluminum deuteride was slowly added to the clear solution A under the protection of nitrogen. During the addition, the temperature of the solution was maintained not higher than 25°C. After the addition of lithium aluminum deuteride was completed, 1.4 g palladium carbon catalyst, after no bubbles emerge in the solution, seal the reaction system, check the airtightness of the device, then replace the gas in the kettle with deuterium gas, after replacing 3 times, fill the autoclave with deuterium gas, When the pressure reaches 1.5MPa, close the inlet valve, stir at a rate of 600rpm and raise the temperature to 45°C. After 24 hours of heat preservation, stop stirring and naturally cool to...

Embodiment 2

[0023] Slowly add 31.3g of hexachlorobenzene into 2800g of anhydrous ether in a dry room temperature environment, and stir at a rate of 250rpm. After stirring for 0.6 hours, a clear solution A is obtained; the clear solution A is transferred to an autoclave with a volume of 6000mL 11.8g of lithium deuteride was slowly added to the clear solution A under the protection of nitrogen. During the addition process, the temperature of the solution was kept not higher than 25°C. After the addition of lithium deuteride was completed, 3.1g of palladium was added to the mixed solution. Carbon catalyst, after no bubbles emerge in the solution, seal the reaction system, check the airtightness of the device, then replace the gas in the autoclave with deuterium gas, after three replacements, fill the autoclave with deuterium gas, when the pressure in the autoclave reaches Close the inlet valve at 3MPa, stir at a rate of 600rpm and raise the temperature to 50°C. After 24 hours of heat preserva...

Embodiment 3

[0025] Slowly add 49.6g of hexabromobenzene into 4000g of anhydrous tetrahydrofuran in a dry room temperature environment, and stir at a rate of 250rpm. After stirring for 1 hour, a clear solution A is obtained; the clear solution A is transferred to an autoclave with a volume of 10L 18.8g of sodium borodeuteride was slowly added to the clear solution A under nitrogen protection. During the addition, the temperature of the solution was maintained not higher than 25°C. After the addition of sodium borodeuteride was completed, 5.0 g palladium carbon catalyst, after no bubbles emerge in the solution, seal the reaction system, check the airtightness of the device, then replace the gas in the kettle with deuterium gas, after replacing 3 times, fill the autoclave with deuterium gas, When the pressure reaches 3MPa, close the inlet valve, stir at a rate of 550rpm and raise the temperature to 65°C. After 24 hours of heat preservation, stop stirring and naturally cool to room temperature...

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Abstract

The invention relates to a preparation method of benzene-d6, and belongs to a synthesis technology of a deuterated compound. The method comprises the following steps: preparing hexahalogenated benzeneinto a clarified solution A; transferring the clarified solution A into an autoclave, and slowly adding a deuteration reagent B into the solution A under the protection of nitrogen to prepare a mixedsolution C; and treating the mixed solution C, and collecting a fraction at 78.8 DEG C to obtain benzene-d6. The reaction realizes the effect of simultaneous deuteration of six reaction sites, repeated operation is not needed, the production period is short, and the method is suitable for industrial scale-up production; the purity of the obtained benzene-d6 is high, and the highest yield can reach 90.6%; and the high-pressure deuterium gas atmosphere promotes the forward proceeding of the reaction, and the use of the catalyst reduces the use amount of the deuterated reagent, reduces the production cost, and can effectively break the dependence of the domestic market on import.

Description

technical field [0001] The invention relates to a preparation method of benzene-d6, which belongs to the synthesis technology of deuterated compounds. Background technique [0002] Benzene-d6 is an organic material with special functions. It has a wide range of applications in explaining the reaction mechanism, elucidating the synthesis pathway, enhancing the stability of drug metabolism, biomedical imaging, gene detection, micro-analysis of metabolites, pesticide residues, and environmental pollutants. application. [0003] Currently, there are two common synthetic methods for benzene-d6. 1. H / D exchange methods: Traditional H / D exchange methods include acid, base or transition metal catalyzed H / D exchange, the disadvantages of these methods include carbon skeleton rearrangement, incompatibility with specific functions, and need for large deuterium sources And expensive catalyst, and the slow or incomplete exchange of deuterium, need repeatedly to carry out H / D exchange o...

Claims

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Application Information

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IPC IPC(8): C07C15/04C07C1/26C07C7/00C07C7/04C07B59/00
CPCC07B59/001C07B2200/05C07C1/26C07C7/005C07C7/04C07C15/04Y02P20/52
Inventor 刘吉平方祝青韩佳
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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