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Method for preparing 2-(5-fluoro-2,4-dinitrophenoxy) acetic acid and ester thereof

A technology of dinitrophenoxy and dinitrobenzene, which is applied in the field of preparation of 2-acetic acid and its esters, can solve problems such as complicated process, low reaction conversion rate and product yield, and high difficulty in industrialization, and achieves reaction yield. The effect of high efficiency and simple process

Inactive Publication Date: 2011-01-19
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, there are three deficiencies in the method for preparing 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid and its esters in the prior art: 1. The process is relatively complicated and industrialization is difficult; 2. The raw materials are relatively expensive or poor in safety; 3. The reaction conversion rate and product yield are low

Method used

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  • Method for preparing 2-(5-fluoro-2,4-dinitrophenoxy) acetic acid and ester thereof
  • Method for preparing 2-(5-fluoro-2,4-dinitrophenoxy) acetic acid and ester thereof
  • Method for preparing 2-(5-fluoro-2,4-dinitrophenoxy) acetic acid and ester thereof

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Experimental program
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Effect test

Embodiment 1

[0027] Preparation of 1,5-difluoro-2,4-dinitrobenzene:

[0028] Add 2,4-difluoronitrobenzene (320g, 2mol) into a 2000mL reaction flask, add 600mL of concentrated sulfuric acid dropwise at room temperature, complete the dropwise addition within 2 hours, start to add 250mL of fuming nitric acid dropwise, add dropwise for 4 hours, add dropwise complete. Insulated at 90°C for 2 hours, poured into ice, filtered, and dried to obtain 400 g (yield 95%) of the title compound, the content of which was greater than 97%.

[0029] 1 H NMR (500Hz, CDCl 3 ): δ8.99(t, 1H, J=7.5Hz), 7.34(t, 1H, J=10Hz)

Embodiment 2

[0031] Preparation of 1,5-difluoro-2,4-dinitrobenzene:

[0032] Add 2,4-difluoronitrobenzene (320g, 2mol) into a 2000mL reaction flask, add 600mL of concentrated sulfuric acid dropwise at room temperature, complete the dropwise addition within 2 hours, start to add 250mL of fuming nitric acid dropwise, add dropwise for 4 hours, add dropwise complete. The reaction was incubated at 95°C for 2 hours, poured into ice, filtered, and dried to obtain 399.6 g (93% yield) of the title compound, with a content greater than 95%.

Embodiment 3

[0034] Preparation of 1,5-difluoro-2,4-dinitrobenzene:

[0035]Add 2,4-difluoronitrobenzene (320 g, 2 mol) to a 2000 mL reaction flask, add 600 mL of concentrated sulfuric acid dropwise at room temperature, and complete the dropwise addition within 2 hours, start adding 250 mL of fuming nitric acid dropwise, and complete the dropwise addition within 4 hours. The reaction was carried out at 100°C for 2 hours, poured into ice, filtered and dried to obtain 399.3 g (90% yield) of the title compound with a content of 92%.

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Abstract

The invention discloses a method for preparing 2-(5-fluoro-2,4-dinitrophenoxy) acetic acid and ester thereof, which comprises two steps of reactions: performing nitration reaction on 2,4-difluoronitrobenzene serving as a starting material to generate 1,5-difluoro-2,4-dinitrobenzene; and performing etherification with glycollic acid or ester thereof to obtain the 2-(5-fluoro-2,4-dinitrophenoxy) acetic acid and the ester thereof, wherein the condensation reaction is completed at the temperature of between -10 and 50 DEG C for 1 to 12 hours under the action of an acid binding agent in an organic solvent.

Description

technical field [0001] The present invention relates to a novel preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid and its esters. Background technique [0002] Flufenazim (quick harvest) is a herbicide absorbed by young shoots and leaves. Used as soil treatment, it can effectively control annual broad-leaved weeds and some grass weeds. It is easy to degrade in the environment and is safe for subsequent crops. . Soybeans and peanuts have good resistance to it. Corn, wheat, barley, rice are moderately tolerant. There are multiple synthetic methods for the synthesis of fluorentrafen, such as Lyga, John W. etc. in Pesticide Science, 1999, 55 (3), 281-287, the synthesis of fluorfen is reviewed; 6-amino-7-fluoro-4-propynyl-1,4-benzo It can be obtained by reacting oxin-3(4H)-one with 3,4,5,6-tetrahydrophthalic anhydride. 6-amino-7-fluoro-1,4-benzo Azin-3(4H)-one and propyne bromide under the action of sodium hydrogen give 6-amino-7-fluoro-4-propynyl-1,4-benzo...

Claims

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Application Information

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IPC IPC(8): C07C205/37C07C201/12C07C205/12C07C201/08
Inventor 王良清吴浩黄民富罗世英绵丽娟田爱俊
Owner NUTRICHEM LAB CO LTD
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