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Synthetic method for stable isotope labeled halobenzene

A technology of stable isotopes and synthesis methods, which is applied in the field of synthesis of stable isotope-labeled halogenated benzenes, can solve the problems of expensive catalysts, strong corrosion, and high risk, and achieve good economy and use value, simple process, and low price. low cost effect

Active Publication Date: 2015-05-13
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the sulfuric acid used in the synthesis of this method is a strong acid, which is highly corrosive, and bromine is generated in the reaction process, which is very dangerous.
Zhang, Lu et al. (Zhang, Lu, Li, Lian-Hua, Wang, Yu-Qi, Yang, Yan-Fang, Liu, Xue-Yuan, Liang, Yong-Min. –1908) using gold chloride as a catalyst, reacting at 80°C for 24h to obtain the target product, the catalyst used in this method is expensive
Wang, Qian et al (Wang, Qian, Deredas, Dariusz, Huynh, Cyril, Schlosser, Manfred. Chemistry-A European Journal, 2003, 9(2), 570–574) and Nappi, Manuel (Nappi, Manuel, Bergonzini, Giulia, Melchiorre, Paolo.Angewandte Chemie-International Edition, 2014, 53(19), 4921–4925.Angew.Chem., 2014, 126(19) 5021–5025.) all reacted with iodine as the halogenating reagent, but Due to the low yield of the reaction, the application of the reaction is limited

Method used

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  • Synthetic method for stable isotope labeled halobenzene
  • Synthetic method for stable isotope labeled halobenzene
  • Synthetic method for stable isotope labeled halobenzene

Examples

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Effect test

Embodiment 1

[0020] A synthetic method for isotope D-labeled halogenated benzene, the method specifically comprises the following steps:

[0021] Mix isotope D-labeled benzene and phosphorus trichloride at a molar ratio of 1:1.1, CuCl and D-labeled benzene at a molar ratio of 1:1, and then place them in acetone. Control the reaction temperature at 90°C and pressure at 1Mpa, and stir the reaction After 12 hours, D-labeled chlorobenzene was obtained. The chemical purity of the obtained product was 99.4%, and the isotopic abundance was 99.0% atom D.

Embodiment 2

[0023] A synthetic method for isotope D-labeled halogenated benzene, the method specifically comprises the following steps:

[0024] Mix isotope D-labeled benzene and phosphorus pentachloride at a molar ratio of 1:1.0, CuI and D-labeled benzene at a molar ratio of 1.5:1, and then place them in dichloromethane. Control the reaction temperature at 60°C and pressure at 2Mpa. The reaction was stirred for 4 hours to obtain D-labeled chlorobenzene with a chemical purity of 99.2% and an isotope abundance of 99.2% atom D.

Embodiment 3

[0026] A synthetic method for isotope D-labeled halogenated benzene, the method specifically comprises the following steps:

[0027] The molar ratio of isotope D-labeled benzene to thionyl chloride is 1:1.5, Fe(NO 3 ) 3 Mix with D-marked benzene at a molar ratio of 0.1:1 and place in acetonitrile, control the reaction temperature at 110°C, pressure 4Mpa, and stir for 24 hours to obtain D-labeled chlorobenzene, which has a chemical purity of 99.2% and isotope-rich The degree is 99.3% atom D.

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Abstract

The invention relates to a synthetic method for stable isotope labeled halobenzene, in particular to a synthetic method for stable isotope D labeled halobenzene-D5 or stable isotope 13C labeled halobenzene-13C6. The organic synthetic method is utilized to enable the stable isotope D labeled benzene-D6 or benzene-13C6 to be reacted with a halogenating reagent, so as to obtain the stable isotope labeled halobenzene-D5 or halobenzene-13C6. Compared with the prior art, the method for preparing the stable isotope labeled halobenzene-D5 or halobenzene-13C6 is simple, safe and reliable; after separation and purification, the chemical purity of the product is up to more than 99.0%, and the isotope abundance is up to more than 99.0% atoms.

Description

technical field [0001] The invention relates to a stable isotope labeling method, in particular to a synthesis method for stable isotope labeling of halogenated benzene. Background technique [0002] Halogenated benzene is one of the most important basic organic chemical raw materials, and can be used for the synthesis of various organic intermediates such as phenol, nitrohalogenated benzene, aniline, and nitrophenol. In isotopic organic synthesis, halogenated benzene is also an extremely important key compound, which is the structural unit of many aromatic ring compounds. Starting from isotope labeling of halogenated benzene, a series of benzene ring-labeled compounds can be obtained, such as: malachite green -D 5 , Leuco Malachite Green-D 5 , ITX-D 3 Wait. There are few public reports on its synthetic methods. [0003] The preparation technology has been monopolized by foreign countries for a long time, which has seriously restricted the development of my country's st...

Claims

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Application Information

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IPC IPC(8): C07C17/12C07C25/06C07C25/02
Inventor 杨超杨维成罗勇李美华潘洁孙雯方超宋家龙吕靖
Owner SHANGHAI RES INST OF CHEM IND
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