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Aryl aniline compound and preparation method thereof

A technology for aryl anilines and compounds, applied in the field of aryl aniline compounds and their preparation, can solve problems such as low reactivity of aryl halides, long coupling reaction time, large steric hindrance of groups, etc., and shorten the reaction time Time, increase yield, increase the effect of reaction rate

Inactive Publication Date: 2019-04-12
SOUTHWEST JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional preparation method of aryl aniline and its derivatives is the coupling reaction of aryl halides and organic boronic acid to prepare aryl aniline compounds. This method has mild reaction conditions and good functional group compatibility, and is widely used in various fields. However, in the traditional synthesis method, the steric hindrance of the group of the aryl halide is large, and the reactivity of the aryl halide is low, so that the amount of the catalyst is large, and the time of the coupling reaction is long.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 50 parts of chlorobenzene, 50 parts of water and 10 parts of aniline into a three-neck round bottom flask, stir evenly with a magnetic force, then add 9 parts of bromine into the reaction kettle at one time, stir for 40 minutes, then take 6 parts of bromine and place it in a burette In the process, take 15 parts of hydrogen peroxide and place it in another burette, install the two burettes on the round bottom flask, and add hydrogen peroxide and bromine dropwise to the round bottom flask at roughly the same speed at the same time. During the dropping process, fully Stir, and after the dropwise addition is completed, leave it to stand to obtain the bromoaniline mixture;

[0021] Take another container, add 50 parts of tetrahydrofuran to the container under an inert atmosphere, raise the temperature of the tetrahydrofuran water bath in the container to 50°C, then add magnesium strips to the reaction kettle, and add p-chlorobromobenzene dropwise to the container while s...

Embodiment 2

[0024] Add 50 parts of bromobenzene, 50 parts of water and 10 parts of aniline into a three-neck round bottom flask, stir evenly with a magnetic force, then add 12 parts of bromine into the reaction kettle at one time, stir for 40 minutes, then take 8 parts of bromine and place it in a burette In the process, take 20 parts of hydrogen peroxide and place it in another burette, install the two burettes on the round bottom flask, and add hydrogen peroxide and bromine dropwise to the round bottom flask at roughly the same speed at the same time. During the dropping process, fully Stir, and after the dropwise addition is completed, leave it to stand to obtain the bromoaniline mixture;

[0025] Take another container, under an inert atmosphere, add 50 parts of diethyl ether into the container, raise the temperature of the diethyl ether water bath in the container to 40°C, then add magnesium strips into the reaction kettle, and add trichlorotoluene dropwise into the container under st...

Embodiment 3

[0028] Add 25 parts of chloroform, 25 parts of dichlorotoluene, 50 parts of water and 10 parts of aniline into a three-neck round bottom flask, stir evenly with a magnetic force, then add 16 parts of bromine into the reaction kettle at one time, stir for 30 minutes, and then take 4 parts Put bromine in the burette, take 20 parts of hydrogen peroxide and put it in another burette, install the two burettes on the round bottom flask, and add hydrogen peroxide and bromine dropwise to the round bottom flask at roughly the same speed at the same time. During the process, fully stir, after the dropwise addition is completed, let stand to obtain the bromoaniline mixture;

[0029] Take another container, add 50 parts of ethylene glycol dimethyl ether into the container under an inert atmosphere, raise the temperature of the ethylene glycol dimethyl ether water bath in the container to 45°C, then add magnesium strips into the reaction kettle, and , add p-bromotoluene dropwise to the con...

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PUM

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Abstract

The invention discloses a preparation method of an aryl aniline compound. The preparation method comprises the following steps of S1, adding an organic solvent, water and aniline into a reaction kettle, adding bromine into the reaction kettle for the first time, and dropwise adding hydrogen peroxide and bromine again; S2, adding an ether solvent into a container in an inert atmosphere, raising thetemperature to 40-50 DEG C, adding magnesium bars into the reaction kettle, dropwise adding aryl halogenated hydrocarbon, adding boric acid ester into another container after dropwise addition of aryl halogenated hydrocarbon is completed, lowering the temperature to -5-5 DEG C, dropwise adding a Grignard reagent into the container, conducting standing to separate liquid, dropwise adding inorganicalkali into an organic phase, extracting the separated liquid, and dropwise adding inorganic acid into an aqueous phase after separation of the liquid, and separating out solids to obtain aryl boricacid; S3, adding aryl boric acid and sodium carbonate in step S2 into the container in step S1, adding a catalyst, and performing a microwave reaction to obtain the aryl aniline compound. Under the action of microwaves, the coupling reaction speed is increased, the reaction time is shortened, and the yield of generated products is increased.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an aryl aniline compound and a preparation method thereof. Background technique [0002] Aromatic amine compounds are an important class of intermediates, widely used in medicine, dyes and other fields. The traditional preparation method of aryl aniline and its derivatives is the coupling reaction of aryl halides and organic boronic acid to prepare aryl aniline compounds. This method has mild reaction conditions and good functional group compatibility, and is widely used in various fields. However, in the traditional synthesis method, the steric hindrance of the group of the aryl halide is large, and the reactivity of the aryl halide is low, so that the consumption of the catalyst is large, and the time of the coupling reaction is long. Contents of the invention [0003] The purpose of the present invention is to solve the above-mentioned deficiencies in ...

Claims

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Application Information

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IPC IPC(8): C07C211/46C07C209/68C07C211/52C07C209/74C07F3/02C07F5/02
CPCC07C209/68C07C209/74C07C211/46C07F3/02C07F5/025C07C211/52
Inventor 蒋亚
Owner SOUTHWEST JIAOTONG UNIV