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Method for synthesizing dibenzyl diselenide

A technology of dibenzyl diselenide and a synthesis method is applied in the field of synthesis of dibenzyl diselenide, can solve the problems of many steps, complicated operation, low yield and the like, and achieves mild reaction conditions, simple operation and high yield high effect

Inactive Publication Date: 2005-09-07
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of these methods are that there are many steps, complex operation, strong base is involved in the reaction, and the yield is low. Directly utilize hydrogen selenide gas

Method used

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  • Method for synthesizing dibenzyl diselenide
  • Method for synthesizing dibenzyl diselenide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the synthesis of dibenzyl diselenide

[0016] Add benzaldehyde (2.5mmol), selenium (2.5mmol), water (2mL), and N,N dimethylformamide 20ml into a 100ml three-necked flask, and introduce CO under normal pressure, control the temperature at 95°C, and stir vigorously with a magnetic force 7 hours (TLC tracking detection). After the reaction is complete, stop passing CO, cool to room temperature, and stir in air for half an hour, add an appropriate amount of water, extract with ether three times, combine the extracts, and evaporate the solvent under reduced pressure. Pass through the column, the eluent is petroleum ether: ethyl acetate (10:1), the eluent is concentrated to obtain the product, m.p.92-93°C, and the yield is 94%.

Embodiment 2

[0018] The reaction temperature is room temperature (19° C.), the reaction time is 7 hours, the experimental method and steps are the same as in Example 1, and the yield is 0%.

Embodiment 3

[0020] The reaction temperature was 60° C., the experimental method and steps were the same as in Example 1, and the yield was 67%.

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Abstract

A method for preparing benzyl selenium ether, comprising putting the aromatic aldchyde, selenium and water into the organic dissolvent, ventilating carbon monoxide into the dissolvent, stirring at the temperature of 50-100 DEG C for 5-15 hours; cooling to normal temperature, extracting with ether, removing the solvent in the tobacco extract in reduced pressure and getting the product. The substituent R of aromatic aldchyde can be a kind of or multiple kinds of electron donating groups and / or electron-attacting groups or hydrogen atom; the consumption between aromatic aldchyde and selenium is 1:1~1.5 in moles, the consumption between aromatic aldchyde and water is 1:1~1:100 in moles, the consumption between reactant and solvent is 1:1~1:500 in moles; the velocity of carbon monoxide bubbling is 20~60 ml / min. The process is simple and being carried out in the same reactor under normal pressure, and gets a high yield.

Description

technical field [0001] The present invention relates to the synthesis of dibenzyl diselenide, which is a process of directly introducing selenium into aromatic molecules. Specifically, under normal pressure and mild conditions, dibenzyl diselenide is obtained through one-step synthesis. Background technique [0002] Diselenide is an important organic synthesis reagent and synthetic intermediate. Such as: the application of dibenzyl diselenide in the synthesis of natural products [J.Org.Chem., 1977, 7, 1228-1230]; the practical application is very wide, and it is used in the solid phase of dibenzyl diselenide in photoconductive materials Separation [document: US 3994791; US3994791; US4013530; GB1508683]; can accelerate the vulcanization of nitrile rubber [Azerb.Khim.Zh., 1985, 1, 73-5 (Russian)]; Cancer Research, 1997, 21, 4757-4764]. The conventional method for synthesizing dibenzyl diselenide has [J.Am.Chem.Soc., 1975,97,5434-5436] by the reaction of chlorinated hydrocar...

Claims

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Application Information

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IPC IPC(8): C07C391/00
Inventor 田丰收余正坤陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI