Preparation method of acifluorfen

A technology of acifluorfen and compounds, which is applied in the field of preparation of acifluorfen, and can solve the problems of harsh synthetic conditions and low yield of acifluorfen

Inactive Publication Date: 2016-05-25
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the existing problems of harsh synthesis conditions and low yield of acifluorfen, and to provide a method for preparing acifluorfen with mild synthesis conditions and high yield

Method used

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  • Preparation method of acifluorfen

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preparation example Construction

[0014] The present invention provides a method for preparing acifluorfen, wherein the acifluorfen is a compound represented by formula (1), wherein the method comprises:

[0015] (1) drop the compound shown in formula (2) in the organic solvent containing alkali metal carbonate and the compound shown in formula (3), make the compound shown in formula (3) and formula (2) show The compound carries out contact reaction, to make the compound shown in formula (4);

[0016] (2) Alkali hydrolysis and acidification of the compound shown in formula (4) to prepare the compound shown in formula (1);

[0017] Formula 1) Formula (2)

[0018] Formula (3) Formula (4)

[0019] Wherein, R is a C2-C6 linear or branched alkyl group.

[0020] According to the present invention, the present invention ingeniously adopts the method of dripping the compound shown in formula (2) so that the compound shown in formula (2) can directly carry out contact reaction with the compound shown in form...

preparation example 1

[0051] 1) Add isopropanol (92g, 1.5mol) dropwise to m-chlorobenzoyl chloride (175g, 1mol) at 80°C. Introduce nitrogen to drive out HCl gas, then remove isopropanol under negative pressure, and keep it at -0.095MPa, 90°C for 2h, and cool down to obtain 198.4g of isopropyl m-chlorobenzoate with a yield of 98.9%.

[0052] 2) Add isopropyl m-chlorobenzoate (150g, 0.748mol) dropwise to fuming nitric acid (480.6g, 7.48mol) at -10°C, and stir at 25°C after the addition is complete (about 3h) After the reaction was completed for 1 h, the reaction product was poured into 960 g of ice water, stirred for 0.5 h, then suction-filtered and the resulting solid was washed with ethanol and then suction-filtered to obtain 141.5 g of the compound shown in formula (3-3). The yield is 78.6%, and the purity is 96%.

preparation example 2

[0054] According to the method described in Preparation Example 1, the difference is that in step 1), ethanol was used instead of isopropanol to obtain 161.4 g of the compound represented by formula (3-1), with a yield of 70.2% and a purity of 97.5%.

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Abstract

The invention relates to the field of herbicides and specifically discloses a preparation method of acifluorfen. The acifluorfen is a compound shown by formula (1) in the specification. The method comprises the following steps: (1) dropwise adding the compound shown by formula (2) in the specification into an organic solvent containing alkali carbonate and the compound shown by formula (3) in the specification so that the compound shown by formula (3) contacts and reacts with the compound shown by formula (2) to obtain the compound shown by formula (4); and (2) performing alkaline hydrolysis and acidification of the compound shown by formula (4) to obtain the compound shown by formula (1). By adopting the preparation method, the target compound can be prepared with relatively high yield in relatively mild reaction conditions.

Description

technical field [0001] The invention relates to the field of herbicides, in particular to a preparation method of acifluorfen. Background technique [0002] Acifluorfen (5-(2-chloro-2,2,2-trifluoro-p-tolyloxy)-2-nitrobenzoic acid, CAS: 50594-66-6) is a contact selective Post-emergence herbicides can be absorbed by the stems and leaves of weeds, and are not easily absorbed by roots in the soil, and are easily decomposed by microorganisms. As a herbicide, acifluorfen is safe for the growth of soybeans, and the main control is broad-leaved grass, so it is especially suitable for controlling amaranth, amaranth, amaranth, ragweed, brassica, ash, wild watermelon, and melon in soybean fields , Datura, split-leaf morning glory, flowering family, rubiaceae, spring Polygonum, Pennsylvania Polygonum, orangutan grass, etc. In addition, it also has a good control effect on green foxtail, millet and wild sorghum at the 1-3 leaf stage, and has a strong inhibitory effect on lettuce and sp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/60
CPCC07C201/12
Inventor 霍世勇吴国林张艳芳金辰路凤奇乔振王大文
Owner NUTRICHEM LAB CO LTD
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