Preparation method for diphenyl diselenium compound

A technology of diphenyldiselenide and compounds, which is applied in the field of organic compound synthesis, can solve the problems of poor substrate universality and achieve the effects of simple operation, simple post-treatment, high yield and purity

Active Publication Date: 2018-05-18
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] This method has poor substrate universality and is only applicable to phenylboronic acid compounds with general electron-donating substituents.

Method used

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  • Preparation method for diphenyl diselenium compound
  • Preparation method for diphenyl diselenium compound
  • Preparation method for diphenyl diselenium compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: Synthesis of p-methoxy diphenyl diselenide

[0039]

[0040] Add p-methoxyarylboronic acid (0.4mmol), elemental selenium (1.2mmol), silver nitrate (0.08mmol), dimethyl sulfoxide (DMSO, 2mL) into the reaction tube, stir at 120°C, pass through a thin The progress of the reaction was monitored by layer chromatography, and the reaction ended after about 2 hours.

[0041] The mixture obtained after the reaction can be further separated and purified, for example: extraction, column chromatography, distillation, decantation, filtration, centrifugation, washing, evaporation, stripping, and adsorption to obtain a relatively pure final product.

[0042] Of course, if necessary, the mixture obtained after the reaction can also be pretreated, such as: concentration, extraction, vacuum distillation, and then introduced into other processes to produce other products, or directly introduced into other processes without pretreatment.

[0043] In this embodiment, the m...

Embodiment 2

[0051] Embodiment 2: Synthesis of m-methoxy diphenyl diselenide

[0052]

[0053] Add 3-methoxyarylboronic acid (0.4mmol), elemental selenium (1.2mmol), silver nitrate (0.08mmol), dimethyl sulfoxide (2mL) into the reaction tube, stir at 120°C, pass through the thin layer Chromatographically monitor the reaction process, after about 2 hours, the reaction ends, add 20mL water and 10mL ethyl acetate to the reaction mixture for extraction, then add anhydrous sodium sulfate to dry, filter after 5min, and wash the filter cake with ethyl acetate (5mL×3 times), then the solvent was spun off, and the product was obtained after separation by column chromatography (petroleum ether as the eluent). After separation and purification, the product was a yellow solid with a yield of 90%.

[0054] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0055] 1 H NMR (500MHz, CDCl 3 )δ8.25(s,2H),7.91(d,J=5.0Hz,2H),7.78(d,J=5.0HZ,2H)7.34(t,J=5.0HZ,2H)...

Embodiment 3

[0059] Embodiment 3: Synthesis of p-chlorodiphenyl diselenide

[0060]

[0061] Add p-chloroarylboronic acid (0.4 mmol), elemental selenium (1.2 mmol), silver nitrate (0.08 mmol), dimethyl sulfoxide (2 mL) into the reaction tube, stir at 120 °C, and monitor the reaction by thin-layer chromatography process, after about 2h, the reaction ends, and 20mL of water and 10mL of ethyl acetate are added to the mixture obtained after the reaction for extraction operation, then anhydrous sodium sulfate is added for drying, and after 5min, the filter cake is washed with ethyl acetate (5mL× 3 times), then the solvent was spinned off, and the product was obtained after separation by column chromatography (the eluent was petroleum ether). After separation and purification, the product was a yellow solid with a yield of 92%.

[0062] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0063] 1 H NMR (500MHz, CDCl 3 ) δ 7.49 (d, J=5.0Hz, 4H), 7.22...

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Abstract

The invention discloses a preparation method for a diphenyl diselenium compound. According to the method, an arylboronic acid compound and elemental selenium serve as reaction raw materials, an organic solvent serves as a reaction solvent, under the effect of a silver catalyst, reaction is carried out so as to obtain the diphenyl diselenium compound, the reaction temperature is 100-140 DEG C, thereaction equation is shown in the specification, wherein R is a benzene ring, a naphthalene ring, a heterocyclic ring or a substituted benzene ring. The method has the beneficial effects that the tolerance of functional groups of substrates is high, and the range of the substrates is wide; and the raw materials and the catalyst are cheap and easily available, the conditions are mild, the post-treatment is simple, the yield and purity of a product are high, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for preparing compounds, in particular to a method for preparing diphenyldiselenide compounds, and belongs to the technical field of organic compound synthesis. Background technique [0002] In 2009, the Braga research group first reported the preparation of symmetrical diaryl (alkyl) diselenides by using nano-copper oxide to catalyze halides and selenium powder. The reaction equation is as follows: [0003] [0004] The method has high chemoselectivity, is compatible with the existence of methoxy, hydroxyl, ester, formyl, bromine atoms, etc., and has mild conditions and a wide range of substrate expansion. [0005] In 2011, Yaming Li et al reported a method for preparing symmetrical diaryl selenides from iodobenzene compounds and elemental selenium under the catalysis of cuprous iodide. The reaction equation is as follows: [0006] [0007] The method adopts elemental selenium as a selenium source, is easy to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/02C07D209/88C07D307/82
CPCC07C391/02C07D209/88C07D307/82
Inventor 刘妙昌杨烨翡赵世宝冷涛黄小波高文霞吴华悦
Owner WENZHOU UNIVERSITY
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