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Aromatic hydrocarbon fluorine ortho-metallization preparation method

A metallization and ortho-position technology, which is applied in the preparation of organic compounds, halogenated hydrocarbons, carbon-based compounds, etc., can solve the problems of high cost of raw materials, high pressure of three wastes treatment, large amount of waste water, etc., and improve the conversion of raw materials low rate effect

Pending Publication Date: 2020-04-17
烟台盛华液晶材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to solve the problem of low reaction yield without adding organic amine in the ortho-position metallization of arene fluorine in the prior art, and after adding organic amine, the problem of large amount of amine-containing waste water is provided. The synthesis method of aromatic hydrocarbon fluorine ortho-position metallation, the present invention uses fluorobenzene derivatives as raw materials, undergoes fluorine ortho-position metallation reaction, and then carries out electrophilic substitution to obtain phenylboronic acids, halogenated benzenes, benzaldehydes and benzene Formic acid and other products solve the problems of large consumption of organic amines, high cost of raw materials, large amount of waste water and high pressure of three wastes treatment in the current production, which is conducive to industrial production

Method used

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  • Aromatic hydrocarbon fluorine ortho-metallization preparation method
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  • Aromatic hydrocarbon fluorine ortho-metallization preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1, a preparation method for the ortho-position metallation of arene fluorine, is to add the compound shown in formula I into an organic solvent, then add a catalytic amount of organic amine, mix well, cool down to below -50°C, and add lithium reagent dropwise , keep warm for 2-3 hours, carry out metallization reaction, after the reaction is completed, add electrophile reagent below -50°C, react with phenyllithium, keep warm for 2-3 hours, and obtain formula II after hydrolysis;

[0026]

[0027] I

[0028]

[0029] II

[0030] In formula Ⅰ, R is C1~C8 straight chain alkanes or C1~C8 straight chain alkoxyls, n=0,1,2, m=0,1, A is hydrogen atom or fluorine atom, B is hydrogen atom or fluorine Atoms, A and B are not fluorine atoms at the same time;

[0031] In formula II, R is C1~C8 straight chain alkane or C1~C8 straight chain alkoxyl, n=0,1,2, m=0,1, A is hydrogen atom or fluorine atom, B is hydrogen atom or fluorine Atoms, A and B are not fluorine atoms ...

Embodiment 2

[0035] Example 2, a preparation method for the ortho-position metallation of arene fluorine, is to add the compound shown in formula I into an organic solvent, then add a catalytic amount of organic amine, mix well, cool down to below -50°C, and add lithium reagent dropwise , keep warm for 2-3 hours, carry out metallization reaction, after the reaction is completed, add electrophile reagent below -50°C, react with phenyllithium, keep warm for 2-3 hours, and obtain formula II after hydrolysis;

[0036]

[0037] I

[0038]

[0039] II

[0040] In formula Ⅰ, R is C1~C8 straight chain alkanes or C1~C8 straight chain alkoxyls, n=0,1,2, m=0,1, A is hydrogen atom or fluorine atom, B is hydrogen atom or fluorine Atoms, A and B are not fluorine atoms at the same time;

[0041] In formula II, R is C1~C8 straight chain alkane or C1~C8 straight chain alkoxyl, n=0,1,2, m=0,1, A is hydrogen atom or fluorine atom, B is hydrogen atom or fluorine Atoms, A and B are not fluorine atoms ...

Embodiment 3

[0044] Example 3, a preparation method for the ortho-position metallation of arene fluorine, is to add the compound shown in formula I into an organic solvent, then add a catalytic amount of organic amine, mix well, cool down to below -50°C, and add lithium reagent dropwise , keep warm for 2-3 hours, carry out metallization reaction, after the reaction is completed, add electrophile reagent below -50°C, react with phenyllithium, keep warm for 2-3 hours, and obtain formula II after hydrolysis;

[0045]

[0046] I

[0047]

[0048] II

[0049] In formula Ⅰ, R is C1~C8 straight chain alkanes or C1~C8 straight chain alkoxyls, n=0,1,2, m=0,1, A is hydrogen atom or fluorine atom, B is hydrogen atom or fluorine Atoms, A and B are not fluorine atoms at the same time;

[0050] In formula II, R is C1~C8 straight chain alkane or C1~C8 straight chain alkoxyl, n=0,1,2, m=0,1, A is hydrogen atom or fluorine atom, B is hydrogen atom or fluorine Atoms, A and B are not fluorine atoms at...

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Abstract

The invention discloses an aromatic hydrocarbon fluorine ortho-metallization preparation method, which comprises the following steps: adding an organic solvent and a catalytic amount of an organic amine into 3-fluoro-(alkyl cyclohexylphenyl) benzene; uniformly mixing, cooling to below -50 DEG C, dropwisely adding a lithium reagent, and carrying out heat preservation for 2-3 hours; and performing ametallization reactions, and after the reaction is finished, adding an electrophilic reagent at a temperature of less than -50 DEG C, reacting with phenyl lithium, carrying out heat preservation for2-3 hours, and hydrolyzing to obtain the 2-fluoro-4-(alkylcyclohexylphenyl) benzene derivative. The method solves the problems of high organic amine consumption, high raw material cost, high wastewater production amount and high three-waste treatment pressure in the current production, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a preparation method for ortho-position metallization of arene fluorine, which belongs to the field of organic chemical synthesis. Background technique [0002] Ortho-metallation of arene fluorine is an important technical method in organic synthesis. Through this reaction, phenylboronic acid compounds, halogenated benzene compounds, benzaldehyde compounds, benzoic acid compounds, etc. can be effectively prepared; the current arene The common means of fluorine ortho-metallation is to use organolithium reagents, carry out hydrogen extraction with the cooperation of equivalent organic amines, and then carry out electrophilic substitution. Organic amine waste water is difficult to treat, and if organic amine is not used, the product conversion yield is low. Under the premise that the country pays more and more attention to environmental protection and the pressure of environmental protection in various places is increasing, resea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/02C07F5/02C07C45/45C07C47/55C07C17/093C07C25/18
CPCC07F1/02C07C17/093C07C45/455C07F5/025C07C25/18C07C47/55
Inventor 刘一李永刚靳灿辉
Owner 烟台盛华液晶材料有限公司
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