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4-cyanobenzyloxy-4'-cyanophenyl ether preparation method

A technology of cyanophenyl ether and cyanobenzyloxy, applied in the field of organic compound preparation, can solve the problems of low yield, harsh conditions and the like, and achieve the effects of high yield, easy product and simple operation conditions

Inactive Publication Date: 2019-09-20
YICHUN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The classic synthetic method is mainly the Williamson method, that is, phenol reacts with sodium hydroxide (or potassium hydroxide, potassium carbonate, etc.) to make sodium phenate (or potassium phenate), and then reacts with halogenated aromatic hydrocarbons. low rate

Method used

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preparation example Construction

[0016] The invention provides a kind of preparation method of 4-cyanobenzyloxy-4'-cyanophenyl ether, comprising the following steps:

[0017] Mix and heat p-cyanobenzyl bromide, 4-cyanophenylboronic acid, sodium hydroxide, hydrogen peroxide solution and water for oxidation and nucleophilic substitution reaction to obtain 4-cyanobenzyloxy-4'-cyanobenzene base ether.

[0018] In the present invention, p-cyanobenzyl bromide, 4-cyanophenylboronic acid, sodium hydroxide, hydrogen peroxide solution and water are mixed and heated, and after oxidation and nucleophilic substitution reaction, 4-cyanobenzyloxy-4'-cyanide is obtained phenyl ether. In the present invention, the dosage ratio of the p-cyanobenzyl bromide, 4-cyanophenylboronic acid, sodium hydroxide, hydrogen peroxide solution and water is preferably 0.1960~1.960g:0.1761~1.763g:0.0640~0.640g: 0.1-1.0mL: 6-60mL, more preferably 0.1960-0.980g: 0.1761-0.8805g: 0.0640-0.320g: 0.1-0.5mL: 6-30mL, more preferably 0.1960g: 0.1761g:...

Embodiment 1

[0030] Add 0.1960g (1mmol) of p-cyanobenzyl bromide, 0.1763g (1.2mmol) of 4-cyanophenylboronic acid, 0.0640g (1.6mmol) of NaOH, H 2 O 6mL, add H under stirring 2 o 2 0.2mL (30%), heated and stirred in an oil bath at 100°C for 8h, the precipitated product precipitated, filtered while hot, dissolved the precipitated product obtained by filtration with ethyl acetate, filtered to remove insoluble matter, added anhydrous sodium sulfate to dry, filtered The desiccant was removed, and the product was crystallized in ethyl acetate to obtain 0.2226 g of pure product with a yield of 95% and a purity of 98%.

[0031] The melting point of the prepared 4-cyanobenzyloxy-4'-cyanophenyl ether was tested by using the automatic melting point instrument of Jinan Haineng Instrument Co., Ltd. model Haineng MP120, and the melting point was 167 ~168°C.

[0032] Adopt the model of German Bruker company to be that the nuclear magnetic resonance instrument of Bruker Avance III (400MHz) type is teste...

Embodiment 2

[0034]According to the method of Example 1 to prepare 4-cyanobenzyloxy-4'-cyanophenyl ether, the difference from Example 1 is that the reaction time is different, and the reaction time in this example is 10h. See Table 1 for the purity and yield of the prepared 4-cyanobenzyloxy-4'-cyanophenyl ether.

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Abstract

The invention provides a 4-cyanobenzyloxy-4'-cyanophenyl ether preparation method, and belongs to the field of preparation of organic compounds. The preparation method comprises: carrying out mixing heating on p-cyanobenzyl bromide, 4-cyanobenzene boronic acid, sodium hydroxide, a hydrogen peroxide solution and water, and carrying out oxidation and nucleophilic substitution reaction to obtain 4-cyanobenzyloxy-4'-cyanophenyl ether. According to the present invention, the target compound is subjected to one-pot synthesis through the oxidation and nucleophilic substitution reaction under the alkaline condition of sodium hydroxide by using H2O2 as the oxidant and by replacing the phenol in the prior art with the 4-cyanobenzene boronic acid, and the gram-level synthesis of the target compound is achieved.

Description

technical field [0001] The invention relates to the field of preparation of organic compounds, in particular to a preparation method of 4-cyanobenzyloxy-4'-cyanophenyl ether. Background technique [0002] 4-cyanobenzyloxy-4'-cyanophenyl ether is an intermediate in organic synthesis and an important building block for the synthesis of biologically active molecules, such as antitrypanosomal drugs and adenosyl ribosyltransferase monodiphosphate inhibitors Wait. The classic synthetic method is mainly the Williamson method, that is, phenol reacts with sodium hydroxide (or potassium hydroxide, potassium carbonate, etc.) to make sodium phenate (or potassium phenate), and then reacts with halogenated aromatic hydrocarbons. The rate is lower. Contents of the invention [0003] In view of this, the invention provides a preparation method of 4-cyanobenzyloxy-4'-cyanophenyl ether. The preparation method provided by the invention can be reacted in pure water to realize gram-level sy...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/54
CPCC07C253/30C07C255/54
Inventor 郭孟萍王翠申秀丽闻永举黄汉弘
Owner YICHUN UNIVERSITY
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