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A kind of chemical synthesis method of 3',4',5'-trifluoro-2-aminobiphenyl

A technology for the chemical synthesis of aminobiphenyls, which is applied in the field of chemical synthesis of 3',4',5'-trifluoro-2-aminobiphenyls, can solve the problems of being unsuitable for industrialized production, and achieve simple and easy operation, The effect of high yield and simple separation and purification

Active Publication Date: 2022-03-25
杭州欧晨科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] This route raw material has adopted expensive catalyst two (acetylacetonate) palladium Pd (acac) 2 (0.67 mol %), reacted at 190°C for 22 h, not suitable for industrial production

Method used

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  • A kind of chemical synthesis method of 3',4',5'-trifluoro-2-aminobiphenyl
  • A kind of chemical synthesis method of 3',4',5'-trifluoro-2-aminobiphenyl
  • A kind of chemical synthesis method of 3',4',5'-trifluoro-2-aminobiphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 Synthesis of 3',4',5'-trifluoro-[1,1'-biphenyl]-2-amine (IV).

[0036] The mass ratio of feeding materials is 3', 4', 5'-trifluoro-2-nitrobiphenyl: aluminum-nickel alloy powder=1: 0.08, and the mass ratio of aluminum and nickel in the aluminum-nickel alloy powder is 53: 47.

[0037] Into a 500 mL autoclave, add 3',4',5'-trifluoro-2-nitrobiphenyl (45.5 g, 0.18 mol), 3.64 g of catalyst aluminum-nickel alloy powder, and triethylamine (36.36 g, 0.36 mol) and absolute ethanol (300 mL), the hydrogen pressure in the kettle is 1.0 MPa, and the temperature is 80 °C, and the reaction is stirred for 8 h. After the reaction was completed, the reaction solution was filtered, and the aluminum-nickel alloy powder was recovered. After the filtrate was concentrated, 200 mL of water and 200 mL of ethyl acetate were added. After stirring at room temperature for 10 min, it was left to stand for stratification. ',4',5'-trifluoro-2-aminobiphenyl 34.9 g, yield 87%. Its materialize...

Embodiment 2

[0038] Example 2 Synthesis of 3',4',5'-trifluoro-[1,1'-biphenyl]-2-amine (IV).

[0039] The mass ratio of feeding materials is 3', 4', 5'-trifluoro-2-nitrobiphenyl: aluminum-nickel alloy powder=1: 0.1, and the mass ratio of aluminum and nickel in the aluminum-nickel alloy powder is 53: 47.

[0040] To a 500 mL autoclave was added 3',4',5'-trifluoro-2-nitrobiphenyl (45.5 g, 0.18 mol), 4.55 g of aluminum-nickel alloy powder, triethylamine (36.36 g, 0.36 mol) and Anhydrous ethanol (300 mL), the hydrogen pressure in the kettle is 1.0 MPa, and the temperature is 90 °C, and the reaction is stirred for 8 h. After the reaction is completed, the reaction solution is filtered, and the aluminum-nickel alloy powder is recovered. After the filtrate is concentrated, water and ethyl acetate are added. 200 mL, stirred at room temperature for 10 min, left to stand for layers, and the organic layer was dried and concentrated to obtain 37.3 g of 3',4',5'-trifluoro-[1,1'-biphenyl]-2-amine, Yield...

Embodiment 3

[0041] Example 3 Synthesis of 3',4',5'-trifluoro-[1,1'-biphenyl]-2-amine (IV).

[0042] The mass ratio of feeding materials is 3', 4', 5'-trifluoro-2-nitrobiphenyl: aluminum-nickel alloy powder=1: 0.5, and the aluminum and nickel mass ratio in the aluminum-nickel alloy powder is 53: 47.

[0043] A 500 mL autoclave was charged with 3',4',5'-trifluoro-2-nitrobiphenyl (45.5 g, 0.18 mol), 22.7 g of aluminum-nickel alloy powder, triethylamine (36.4 g, 0.36 mol) and Anhydrous methanol (300 mL), the hydrogen pressure in the kettle was 1.0 MPa, and the temperature was 80 °C, and the reaction was stirred for 8 h. After the reaction was completed, the reaction solution was filtered, and the aluminum-nickel alloy powder was recovered. After the filtrate was concentrated, water and ethyl acetate were added. 200 mL, stirred at room temperature for 10 min, left to stand for layers, and the organic layer was dried and concentrated to obtain 37.3 g of 3',4',5'-trifluoro-2-aminobiphenyl (IV) w...

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Abstract

The invention discloses a chemical synthesis method of 3',4',5'-trifluoro-2-aminobiphenyl, which uses 3,4,5-trifluorobromobenzene as a starting material, and undergoes formatting reactions in sequence , borylation reaction and coupling reaction to obtain 3',4',5'-trifluoro-2-nitrobiphenyl, 3',4',5'-trifluoro-2-nitrobiphenyl and then through catalytic reduction The reaction yields the target product 3',4',5'-trifluoro-2-aminobiphenyl. The invention provides a new synthesis route of the compound 3',4',5'-trifluoro-2-aminobiphenyl, which has the advantages of simple process operation, mild reaction conditions, high yield and simple separation and purification. Among them, in the synthesis process of 3',4',5'-trifluoro-2-nitrobiphenyl, the amount of catalyst is low, which reduces the production cost and is more suitable for large-scale industrial application.

Description

technical field [0001] The invention relates to a chemical synthesis method of 3', 4', 5'-trifluoro-2-aminobiphenyl. Background technique [0002] 3',4',5'-trifluoro-2-nitrobiphenyl is an important chemical synthesis raw material, which can be used to synthesize a new fungicide fluconazole. Fluoxapyr is a new amide pyrazole succinate dehydrogenase inhibitor with both control and prevention effects. It can inhibit the respiration of fungi, inhibit spore germination, germ tube elongation, mycelium growth and spore formation, and can control a variety of fungal diseases of various crops. It is mainly used in fruit trees, vegetables, rapeseed and soybeans. Control apple scab, powdery mildew, cherry leaf spot, peach blight and powdery mildew. So far, many literatures and patents have reported the synthesis of fluoxamid, mainly including WO2017140593; Britton et al., Eur. J. Org. Chem., 2017, 44, 6566-6574; WO2016016298, etc. [0003] 3',4',5'-trifluoro-2-nitrobiphenyl: its mol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/36C07C211/52
Inventor 李振华张旭超谭志勇
Owner 杭州欧晨科技有限公司