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Synthesis method of 3', 4', 5 '-trifluoro-2-nitro-1, 1'-biphenyl

A synthetic method and technology of nitrochlorobenzene, applied in chemical instruments and methods, preparation of organic compounds, organic compound/hydride/coordination complex catalysts, etc., can solve unrealistic industrial production, large consumption, catalyst No problems such as commercialization have been realized, and the effect of good industrial application production scene, high income, and low equipment requirements has been achieved

Pending Publication Date: 2020-09-01
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this reaction, the catalyst is also not commercialized, and the amount used is large
In addition, at present, it seems that microwave reactors are basically not realistic to realize industrial production.
[0006] Therefore, the development of a possible method that can solve the deficiencies in the prior art and realize the industrial synthesis of 3', 4', 5'-trifluoro-2-nitro-1,1'-biphenyl has also become a priority for those skilled in the art. Important pursuit, but so far unresolved puzzle

Method used

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  • Synthesis method of 3', 4', 5 '-trifluoro-2-nitro-1, 1'-biphenyl
  • Synthesis method of 3', 4', 5 '-trifluoro-2-nitro-1, 1'-biphenyl
  • Synthesis method of 3', 4', 5 '-trifluoro-2-nitro-1, 1'-biphenyl

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Experimental program
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Effect test

specific Embodiment 1

[0029] A kind of synthetic method of 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl, comprising the steps:

[0030] S1. Under nitrogen protection, mix 2-nitrochlorobenzene, 3,4,5-trifluorophenylboronic acid, a catalyst, an alkaline substance and a reaction solvent, and then react at 100° C. for 24 hours to obtain a reaction solution;

[0031] S2. Post-treat the reaction solution obtained in step S1 to obtain 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl, that is, after stopping the reaction, naturally cool to room temperature , adding water (500mL), a large amount of solids were precipitated, suction filtered and washed with water to obtain solids; the same operation was repeated several times for the aqueous phase. The solids were combined and treated by beating with ethyl acetate and petroleum ether to obtain about 232.8 g of a light yellow solid with a total yield of about 92% and a liquid phase purity >98%.

[0032] The NMR data of the product are as follows: 1 H NMR (400MHz, CDCl ...

specific Embodiment 2

[0041] A kind of synthetic method of 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl, comprising the steps:

[0042] S1. Under the protection of argon, mix 2-nitrochlorobenzene, 3,4,5-trifluorophenylboronic acid, a catalyst, an alkaline substance and a reaction solvent, and then react at 40°C for 24 hours to obtain a reaction solution;

[0043] S2. Post-treat the reaction solution obtained in step S1 to obtain 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl. By calculation, the total yield of the reaction is 60%, liquid phase purity 94%.

[0044] Further, the reaction solvent is tetrahydrofuran.

[0045] Further, the alkaline substance is sodium carbonate.

[0046] Further, the catalyst is a complex shown in formula (2):

[0047]

[0048] Further, the molar ratio of 2-nitrochlorobenzene, 3,4,5-trifluorophenylboronic acid, catalyst, and basic substance is 1:1:0.004:1,

[0049] The amount of the reaction solvent used is 5 ml / g based on the mass of 2-nitrochlorobenzene.

[0050] Furthe...

specific Embodiment 3

[0052] A kind of synthetic method of 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl, comprising the steps:

[0053]S1. Under the protection of helium, mix 2-nitrochlorobenzene, 3,4,5-trifluorophenylboronic acid, catalyst, basic substance and reaction solvent, and then react at 100°C for 3 hours to obtain a reaction solution;

[0054] S2. Post-treat the reaction solution obtained in step S1 to obtain 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl. By calculation, the total yield of the reaction is 94%, liquid phase purity >98%.

[0055] Further, the reaction solvent is 2-methyltetrahydrofuran.

[0056] Further, the alkaline substance is potassium carbonate.

[0057] Further, the catalyst is a complex shown in formula (3):

[0058]

[0059] Further, the molar ratio of 2-nitrochlorobenzene, 3,4,5-trifluorophenylboronic acid, catalyst, and basic substance is 1:2:0.000005:3,

[0060] The amount of the reaction solvent used is 15 ml / g based on the mass of 2-nitrochlorobenzene.

[0061] ...

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Abstract

The invention discloses a synthesis method of 3', 4', 5 '-trifluoro-2-nitro-1, 1'-biphenyl, which comprises the following steps: S1, under the protection of nitrogen or inert gas, mixing 2-nitrochlorobenzene, 3, 4, 5-trifluorophenylboronic acid, a catalyst, an alkaline substance and a reaction solvent, and performing a reaction at 40-100 DEG C for 3-24 hours to obtain a reaction solution; and S2,carrying out post-treatment on the reaction liquid obtained in the step S1, so as to obtain 3', 4', 5 '-trifluoro-2-nitro-1, 1'-biphenyl. The method has the following beneficial effects that 1, 2-nitrochlorobenzene is simple, easy to obtain and low in price, and the production cost is reduced; 2, the catalyst is stable, easy to obtain and low in catalytic amount, the operation steps are greatly simplified, and the production cost is saved; 3, reaction conditions are mild, requirements on equipment are low, and the method has the advantage that relatively high benefits can still be kept under the condition that the use amount of the catalyst is very small; and 4, the highest yield of the product is basically quantified.

Description

technical field [0001] The invention relates to a synthesis method of 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl, which belongs to the field of organic chemical synthesis. Background technique [0002] Fluxapyroxad is an active ingredient of a new type of fungicide developed by BASF, which can be used to prevent and control broad-spectrum fungal diseases. Among them, 3',4',5'-trifluoro-2-nitro-1,1'-biphenyl is an important intermediate for the synthesis of flufenapyramide, and its structural formula is: [0003] [0004] Transition metal-catalyzed coupling reactions are the main method for the synthesis of 3’,4’,5’-trifluoro-2-nitro-1,1’-biphenyl. Currently, there are some reports on the synthesis of this intermediate in the literature. However, in the current reports, some complex catalysts (such as air-sensitive, easily oxidized and degraded catalysts in the air), self-made non-commercialized catalysts, relatively high-priced raw materials or complex reaction conditions...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/12B01J31/22
CPCC07C201/12B01J31/2295B01J2531/824B01J2231/4227B01J2531/0233C07C205/12
Inventor 邵黎雄金开郎童年陆建梅
Owner WENZHOU UNIVERSITY
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