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Process for preparing benzo selenophen compound by catalytic method

A technology of benzoselenophene and compounds, which is applied in the field of preparation of heterocyclic compounds, can solve the problems of low reaction yield, high cost, and expensive Se-containing compounds, and achieve simple operation, short reaction cycle, and good scalability Effect

Active Publication Date: 2019-11-22
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The catalyst used in this method is iron salt, which is cheap and easy to get, but the Se-containing compound is expensive, the cost is high, and the reaction yield is not high

Method used

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  • Process for preparing benzo selenophen compound by catalytic method
  • Process for preparing benzo selenophen compound by catalytic method
  • Process for preparing benzo selenophen compound by catalytic method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the impact of different catalyst additions on synthetic effect

[0035] During the preparation process, we tried a variety of catalysts, and finally determined that silver oxide had the best catalytic effect. Using this catalyst not only improved the reactivity of raw materials, but also promoted the forward progress of the reaction; then we The addition ratio of the catalyst was also tested, see Table 1 for details.

[0036] Table 1 The influence of different catalyst additions on the synthesis effect

[0037] serial number Ag 2 O, mol%

[0038] In the presence of 2-(phenylethynyl)benzoselenide (2mmol) as the raw material, silver oxide as the catalyst, and acetic acid (20ml) as the solvent, stir at room temperature (25°C) for 1.5h, then add 50mL of 1M Sodium hydroxide solution, extracted with 2x30mL dichloromethane, combined the organic phases, dried overnight with anhydrous sodium sulfate or anhydrous magnesium sulfate, spin-dried, and pas...

Embodiment 2

[0039] Embodiment 2: the influence of different acidic solvents on synthetic effect

[0040]In the previous research, we preliminarily characterized the solvent as an acidic solvent, and the acidic solvent can well guide the forward reaction (that is, 2-ethynyl benzoselenide derivative → benzoselenophene compound); In the experiment, we used the same raw materials and reaction time to conduct experiments in solvent systems composed of different acids, and comprehensively considered the indicators such as the time of reaction end point in different systems, the stability of the compound, and the purity of the compound, combined with Table 2 , the results show that: the use of acetic acid and trifluoroacetic acid to guide the effect of the reaction is the best, at this time, the reaction is kept under acidic conditions, silver oxide and raw materials can be fully contacted.

[0041] The influence of table 2 different acidic solvents on synthetic effect

[0042] serial...

Embodiment 3

[0048] Embodiment 3: 2-(phenylethynyl) benzoselenophene (A 1 ) preparation

[0049] Add 2-(phenylethynyl)benzoselenide (542.4mg, 2mmol), silver oxide (23.1mg, 0.1mmol), acetic acid (20mL) in turn to a 25mL round bottom flask, and stir the reaction at room temperature (25°C) for 1.5 hours , then add 50mL of 1M sodium hydroxide solution to the reaction system, extract with 2x30mL dichloromethane, combine the organic phases, dry overnight with anhydrous sodium sulfate or anhydrous magnesium sulfate, spin dry, use petroleum ether: ethyl acetate = 50 : 1 through the column to obtain 473.2 mg of the target compound as a white solid with a yield of 92%.

[0050] The product structure is: That 1 H spectrum, 13 C spectrum see Figure 1A , 1B . 2-phenylbenzo[b]selenophene

[0051] 1 H NMR (400MHz, CDCl 3 )δ7.92(dd, J=7.9,1.2Hz,1H),7.82(dd,J=7.9,1.2Hz,1H),7.76(s,1H),7.72–7.66(m,2H),7.48–7.44 (m,2H),7.43–7.38(m,2H),7.33–7.26(m,1H);

[0052] 13 C NMR (101MHz, CDCl 3 )δ147.72...

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Abstract

The invention provides a process for preparing a benzo selenophen compound by a catalytic method, and belongs to the technical field of heterocyclic compound preparation. The method comprises the following steps of in the presence of an acidic solvent, taking the silver oxide as a catalyst and a 2-ethynylbenzyl selenide derivative as a raw material, completely reacting at (10-40) DEG C in one step, neutralizing, extracting and spin-drying to obtain a crude product, and carrying out column chromatography separation to obtain the high-quality benzo selenophen compound. The preparation steps aresimple and short, the reaction conditions are mild, the product yield is high, the cost is low, and a universal new method is provided for the preparation of the benzo-selenophen compound.

Description

technical field [0001] The application relates to a process for preparing benzoselenophene compounds by a catalytic method, which belongs to the technical field of preparation of heterocyclic compounds. Background technique [0002] As one of the simplest five-membered aromatic heterocycles, selenophene has important applications in organic synthesis, conductive materials and nonlinear optical materials. As an important derivative of selenophene, benzoselenophene has a good application prospect in the synthesis of new materials such as liquid crystal polymers and superconductors. [0003] The present invention reports a new method for synthesizing benzoselenophene compounds using 2-ethynyl benzyl selenide derivatives as raw materials. At present, the common preparation methods using this compound as a raw material are as follows: [0004] (1) Using 2-ethynyl phenyl selenide derivatives as raw materials, dichloromethane or chloroform as a solvent, and halogen (bromine or io...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D345/00
CPCC07D345/00
Inventor 蔡涛沈润溥徐慧婷吴春雷高晓忠丰诚杰罗蒙强
Owner SHAOXING UNIVERSITY
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