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Pyrocatechol derivative and preparation method thereof

A technology of catechol and derivatives, applied in the field of catechol derivatives and their preparation, can solve the problems of being difficult to realize to mass production, difficult to realize, etc., and achieve a wide range of substrates, convenient operation, and shortening The effect of the synthesis process

Inactive Publication Date: 2018-06-15
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in many literatures that the introduction of DG is relatively easy, but the conditions for removing DG are quite harsh. For example, these conditions generally require the use of particularly active metals such as sodium or potassium, and they are still under high temperature conditions. In these literatures, a lot of risk factors have been subtly added to the experiment. What is more serious is that the conditions of these reactions are difficult to achieve in the stage of mass production in practical application. If the company follows this traditional old method to In terms of operation, even small batches of gram-level reactions are difficult to achieve

Method used

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  • Pyrocatechol derivative and preparation method thereof
  • Pyrocatechol derivative and preparation method thereof
  • Pyrocatechol derivative and preparation method thereof

Examples

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Effect test

Embodiment 1

[0033] Embodiment 1, the preparation method of synthesizing 2-((5-nitropyrimidin-2-yl) oxygen group) phenyl acetate

[0034] The first step: vacuumize a dry 50ml reaction eggplant bottle with nitrogen three times, then add phenol (0.0941mg, 1.0mmol, 1.0equiv) to the reaction eggplant bottle, add 3.0ml of dried THF and stir until the phenol is completely Then add NaH (28.8mg, 1.2mmol, 1.2equiv, 60% suspension in mineral oil) to the reaction eggplant bottle under ice bath, and react for 30min under ice bath; then add 2-chloro- 5-Nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv). The whole mixture was slowly raised to 50°C for 12 hours. The process of the reaction was detected by TLC, if it was detected that all the phenol had reacted completely, the reaction could be stopped. The experimental treatment is to drain the solution in the reaction; dissolve the solute in the reaction eggplant bottle with ethyl acetate, and transfer it to a 100ml round bottom flask, and add 3ml (200-3...

Embodiment 2

[0046] Embodiment 2, the method for the preparation of synthetic 2-((5-nitropyrimidin-2-yl) oxy)phenyl acetate

[0047] The first step: vacuumize a dry 50ml reaction eggplant bottle with nitrogen three times, then add 4-tert-butylphenol (0.150g, 1.0mmol, 1.0equiv) to the reaction eggplant bottle, and add 3.0ml of dried Stir in THF until 4-tert-butylphenol is completely dissolved, then add NaH (28.8mg, 1.2mmol, 1.2equiv, 60% sodium hydride content suspended in mineral oil) to the reaction bottle under ice bath. React under ice bath for 30min; then add 2-chloro-5-nitropyrimidine (0.1593g, 1.0mmol, 1.0equiv) into the reaction flask. The whole mixture was slowly raised to 50°C for 12 hours. The process of the reaction was detected by TLC, if it was detected that all the phenol had reacted completely, the reaction could be stopped. The experimental treatment is to drain the solution in the reaction; dissolve the mixture in the reaction eggplant bottle with ethyl acetate, and tran...

Embodiment 3

[0052] Embodiment 3, the method for the preparation of synthetic 3-(tert-butyl)-2-((5-nitropyrimidin-2-yl)oxy)phenyl acetate

[0053] Step 1: Vacuum a dry 50ml reaction flask with nitrogen three times, then add 2-tert-butylphenol (150mg, 1.0mmol, 1.0equiv) to the reaction flask, add 3.0ml of dried THF Stir until 2-tert-butylphenol is completely dissolved, then add NaH (28.8mg, 1.2mmol, 1.2equiv, 60% sodium hydride content suspended in mineral oil) to the reaction bottle under ice bath, and store in ice bath React for 30 min; then add 2-chloro-5-nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv) into the reaction bottle. The whole mixture was slowly raised to 50°C for 12 hours. The process of the reaction was detected by TLC, if it was detected that all the phenol had reacted completely, the reaction could be stopped. The experimental treatment is to drain the solution in the reaction; dissolve the solute in the reaction eggplant bottle with ethyl acetate, and transfer it to a 1...

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Abstract

The invention discloses a pyrocatechol derivative and a preparation method of the derivative. The preparation method of the derivative comprises the following steps of: (1) taking an aryl phenol compound as a substrate, and 2-chlorine-5-nitryl pyrimidine as an orienting group, slowly adding a redistilled tetrahydrofuran solvent ice bath into sodium hydride in the presence of nitrogen for reactionto form a pyrimidine aryl phenol compound intermediate, (2) taking iodobenzene diacetate as an oxidant and palladium acetate as a catalyst, catalyzing the pyrimidine aryl phenol compound intermediatefor C-H activating reaction in a solvent, performing swab-off, and chromatographic separation and purification to form an acetoxylated phenylamine derivative, and (3) allowing the acetoxylated phenylamine derivative to react in a tetrahydrofuran solvent by using hydrazine hydrate, and performing quenching, washing, extraction, drying, swab-off, and chromatographic separation and purification to form an ortho-aminophenol derivative. The first two steps of the method can be achieved in a pot, and small-scale production of above a 'gram' level can be even achieved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a class of catechol derivatives and a preparation method thereof. Background technique [0002] In recent years, with the rise of transition metal-catalyzed C–H bond functionalization, directing groups assist C sp2 -H bond functionalization has attracted extensive attention. Various directing groups such as amines, imines, oximes, diazenes, amides, pyridines, pyrimidines, carboxylic acids, etc., were used to achieve regioselective C–H functionalization. Although the introduction and removal of the introducing group usually adds two steps to the overall synthesis, it can become more manipulable if the directing group (DG) is only briefly attached to the substrate molecule during the functionalization step. However, only very limited success examples have been obtained, and only a few reports have been recorded, and the substrates are limited to amines and formaldehy...

Claims

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Application Information

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IPC IPC(8): C07C37/055C07C39/08C07D239/34C07C39/24
CPCC07C37/0555C07C39/08C07C39/245C07D239/34
Inventor 冯鹏举陈填烽陈俊丰黄译锋
Owner JINAN UNIVERSITY
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