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Synthesis method of aryl selenide compound

A technology of ether compound and synthesis method, which is applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of unfavorable industrial expansion, difficult product processing, etc., and achieve low environmental pollution, good tolerance, and high yield Effect

Inactive Publication Date: 2022-01-14
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The problem of this method is the same as the above method, the reaction needs to be completed under high temperature and the participation of metal catalysts, which brings difficulties to the later product processing
Not conducive to the expansion of industry

Method used

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  • Synthesis method of aryl selenide compound
  • Synthesis method of aryl selenide compound
  • Synthesis method of aryl selenide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1 Synthesis of p-methoxyphenyl selenide.

[0074] Add 30.4 mg of p-methoxyphenylboronic acid, 23 μL of MeSeSeMe, 66 mg of tetra-n-butylammonium tetrafluoroborate and 10 mL of acetonitrile into a three-port reaction tube equipped with a magnetic stirring bar. In the air, under the condition of 50° C., the electricity was reacted for 3 hours, and the constant current was 6 mA. After the reaction was completed, it was simply filtered, concentrated by rotary evaporation and put on the column. Using pure petroleum ether and 3% ethyl acetate as the mobile phase in turn, 34.8 mg of p-methoxybenzyl selenide was obtained with a yield of 86%.

[0075] Product p-methoxybenzyl selenide: 1 H NMR (400MHz, CDCl 3 ): δ7.41(d, J=8.8Hz, 2H), 6.82(d, J=8.8Hz, 2H), 3.79(s, 3H), 2.30(s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ158.7, 133.4, 121.5, 114.8, 55.3, 8.7.

Embodiment 2

[0076] Example 2 Synthesis of m-methoxybenzyl selenide.

[0077] Add 30.4 mg of m-methoxyphenylboronic acid, 23 μL of MeSeSeMe, 66 mg of tetra-n-butylammonium tetrafluoroborate and 10 mL of acetonitrile into a three-port reaction tube equipped with a magnetic stirring bar. In the presence of air at 50°C, the reaction was carried out with electricity for 3 hours, and the constant current was 6mA. After the reaction was completed, it was simply filtered, concentrated by rotary evaporation, and put on the column. Using pure petroleum ether and 3% ethyl acetate as mobile phases in turn, 24.3 mg of m-methoxybenziselenide was obtained with a yield of 60%.

[0078] The product m-methoxybenzyl selenide: 1 H NMR (400MHz, CDCl 3 ): δ7.18(t, J=8.0Hz, 1H), 7.00(d, J=8.4Hz, 1H), 6.97(s, 1H), 6.74(dd, J=2.4, 2.0Hz, 1H), 3.80 (s,3H),2.36(s,3H). 13 C NMR (100MHz, CDCl 3 ): δ159.8, 133.0, 129.8, 122.4, 115.7, 111.7, 55.2, 7.1.

Embodiment 3

[0079] Example 3 Synthesis of o-methoxybenzyl selenide.

[0080] Add 30.4 mg of o-methoxyphenylboronic acid, 23 μL of MeSeSeMe, 66 mg of tetra-n-butylammonium tetrafluoroborate and 10 mL of acetonitrile into a three-port reaction tube equipped with a magnetic stirring bar. In the presence of air at 50°C, the reaction was carried out with electricity for 3 hours, and the constant current was 6mA. After the reaction was completed, it was simply filtered, concentrated by rotary evaporation and put on the column. Using pure petroleum ether and 5% ethyl acetate as the mobile phase in turn, 27.5 mg of o-methoxybenziselenide was obtained with a yield of 68%.

[0081] The product o-methoxybenzyl selenide: 1 H NMR (400MHz, CDCl 3 ): δ7.24(d, J=7.6Hz, 1H), 7.19(t, J=8.0Hz, 1H), 6.94(t, J=7.6Hz, 1H), 6.82(d, J=8.0Hz, 1H ),3.89(s,3H),2.28(s,3H). 13 CNMR (100MHz, CDCl 3 ): δ128.4, 126.7, 121.5, 121.2, 110.0, 55.8, 4.8.

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Abstract

The invention discloses a synthesis method of an aryl selenide compound, wherein the method comprises the steps: in a MeCN acetonitrile solvent, under the air condition of 50 DEG C, taking current as a reaction driving agent, taking tetrabutylammonium tetrafluoroborate nBu4BF4 as an electrolyte, and taking arylboronic acid and ResSeR diaryl diselenide as reaction raw materials, carrying out substitution reaction to prepare the aryl selenide compound. Compared with an existing synthesis method of an aryl selenide compound, the method disclosed by the invention has the obvious advantages of cheap and easily available reaction raw materials, small environmental pollution, good tolerance to various functional groups of aromatic rings, heterocyclic rings and fat alkanes, high yield and the like, and can be widely applied to synthesis in the fields of medicines, materials, natural products and the like in the industrial circle and the academic circle.

Description

technical field [0001] The invention relates to the technical field of synthesis and preparation of a class of chemical products, in particular to a synthesis method of an aryl selenide compound. Background technique [0002] Organoselenium compounds hold great promise not only as versatile synthetic intermediates that facilitate the generation of more complex molecules, but also as fundamental structural components in a plethora of functional materials and potential drug candidates. For example, several aryl selenide moieties with N- or O-substituents on the aromatic rings have been shown to have anti-Alzheimer's disease, anti-tubulin and cytotoxic activities, as well as 5-lipoxygenase inhibitory effect. Therefore, the synthesis of related aryl selenide compounds has important theoretical significance and industrial practical value. [0003] At present, the method for synthesizing aryl aryl selenide compound has: [0004] Method 1, using the traditional method to realize...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/01
CPCC25B3/01
Inventor 付拯江蔡琥尹健何冬冬
Owner NANCHANG UNIV
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