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Preparation method of 3,4,5-trifluoro-2'-nitrobiphenyl

A technology of nitrobiphenyl and o-chloronitrobenzene, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve problems such as insufficient environmental protection, and achieve improved reaction safety, simple handling, and reduced The effect of energy consumption

Active Publication Date: 2019-07-02
ZHEJIANG RES INST OF CHEM IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of this method is about 86-97%, but it requires high temperature and high pressure reaction, and there are certain safety hazards, and tetrahydrofuran is used as an organic solvent, which is not environmentally friendly enough

Method used

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  • Preparation method of 3,4,5-trifluoro-2'-nitrobiphenyl
  • Preparation method of 3,4,5-trifluoro-2'-nitrobiphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add o-chloronitrobenzene (compound Ⅰ) 1.57g, 3,4,5-trifluorophenylboronic acid (compound Ⅱ) 1.94g, palladium chloride 8.8mg (0.5mol%) and SPhos (2-bicyclic Hexylphosphine-2',6'-dimethoxybiphenyl) 41mg (1mol%), add 2% phase transfer catalyst compound IV (wherein R=CH 3 , n=15) of aqueous solution 20mL, replace nitrogen in the system, add 1.66mL (1.2eq) of triethylamine, the system becomes clear, stir and react at 25°C for 8h, there are many solids precipitated in the system, filter, then use 2% HCl Wash with water and dry to obtain 2.15 g of 3,4,5-trifluoro-2'-nitrobiphenyl with a yield of 85% and a purity of 98.5% by HPLC.

Embodiment 2

[0050] Add 1.57 g of o-chloronitrobenzene (compound Ⅰ), 1.94 g of 3,4,5-trifluorophenylboronic acid (compound Ⅱ), 8.8 mg of palladium chloride (0.5 mol%) and XPhos (2-di Cyclohexylphosphonium-2', 4', 6'-triisopropylbiphenyl) 47mg (1mol%), add 2% phase transfer catalyst compound IV (wherein R=CH 3 , n=15) of aqueous solution 20mL, replace nitrogen in the system, add 1.66mL (1.2eq) of triethylamine, the system becomes clear, stir and react at 25°C for 8h, there are many solids precipitated in the system, filter, then use 2% HCl Wash with water and dry to obtain 2.23 g of 3,4,5-trifluoro-2'-nitrobiphenyl with a yield of 88% and a purity of 98.8% by HPLC.

Embodiment 3

[0052]Add 1.57g of o-chloronitrobenzene (compound Ⅰ), 1.94g of 3,4,5-trifluorophenylboronic acid (compound Ⅱ), 11.2mg of palladium acetate (0.5mol%) and SPhos (2-bicyclohexyl Phosphine-2',6'-dimethoxybiphenyl) 41mg (1mol%), add 2% phase transfer catalyst compound IV (wherein R=CH 3 , n=15) of aqueous solution 20mL, replace nitrogen in the system, add 1.66mL (1.2eq) of triethylamine, the system becomes clear, stir and react at 25°C for 8h, there are many solids precipitated in the system, filter, then use 2% HCl Wash with water and dry to obtain 2.14 g of 3,4,5-trifluoro-2'-nitrobiphenyl with a yield of 85% and a purity of 98.1% by HPLC.

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Abstract

The invention discloses a preparation method of 3,4,5-trifluoro-2'-nitrobiphenyl. The method comprises the following steps: water is used as a solvent, o-chloronitrobenzene and 3,4,5-trifluorobenzeneboronic acid are subjected to a reaction in the presence of a phase transfer catalyst under the action of an acid binding agent, a catalyst and a ligand of the catalyst, and therefore the 3,4,5-trifluoro-2'-nitrobiphenyl is obtained. The method provided by the invention adopts pure water phase reaction, and has the advantages of greenness, environmental protection and convenient post-treatment.

Description

technical field [0001] The invention belongs to the field of synthesis of pesticide intermediates and relates to a preparation method of 3,4,5-trifluoro-2'-nitrobiphenyl. Background technique [0002] Flufenapyramide is a new type of fungicide discovered and produced by BASF. It has the advantages of high efficiency, broad spectrum, long-lasting effect and strong selectivity. It can inhibit spore germination, spore tube elongation, mycelium growth and spore formation. , can effectively prevent and control major diseases of grains, soybeans, corn, rapeseed and special crops. In 2011, fluxapyroxad was first registered and marketed in the UK, and it is now registered and marketed in Australia, the United States, Canada, 13 EU countries, Brazil and China, and plans to introduce it to more than 50 other countries for use in more than 100 countries. grow crops. For BASF, the annual peak sales of flufenapyramide can reach 600 million euros. [0003] The important intermediate fo...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/12
CPCC07C201/12C07C205/12
Inventor 李晶沈方烈韦伟张晓铭
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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