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Preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetate

A technology of dinitrophenoxy and dinitrophenol, which is applied in the field of preparation of 2-acetate, can solve problems such as poor safety, complicated process, and difficult industrialization, and achieve low production cost, simple reaction, and easy operation Effect

Active Publication Date: 2018-12-11
安徽宁亿泰科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In summary, the prior art has the following problems in the preparation of ethyl 2-(5-fluoro-2,4-dinitrophenoxy)acetate: 1. The process is complicated and industrialization is difficult; 2. The raw materials are relatively expensive or poor in safety; 3. The reaction conversion rate is low and the product purity is low

Method used

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  • Preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetate
  • Preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetate

Examples

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Effect test

Embodiment 1

[0036] Step 1, add 99g of water into a 250mL reaction kettle at room temperature, slowly add 9.7g (0.17mol) of KOH under magnetic stirring, cool down in an ice-water bath, and then add 1,5-difluoro-2,4-dinitrobenzene (15g , 73.5mmol) was dissolved in 25mL of tetrahydrofuran, and the solution was placed in a constant pressure dropping funnel and slowly added dropwise to the reaction kettle, and a clear light yellow system was obtained after dropping. In the post-processing step, 18g (0.17mol) of 36% HCl was still added dropwise under an ice-water bath. After the dropwise addition, THF was evaporated under reduced pressure, and a large amount of beige solid was precipitated after cooling down. After filtration and drying, 13.5g of solid was obtained, with a yield of 91% and a purity of 99%. %.

[0037] Step 2, 5-fluoro-2,4-dinitrophenol (50.5g, 0.25mol), ethyl chloroacetate (30.5g, 0.25mol), 1,1,1-methyl trichloroacetate (53.2g , 0.3mol), potassium carbonate (0.69g, 5mmol), a m...

Embodiment 2

[0039] Step 1, add 75g of water into a 250mL reaction kettle at room temperature, slowly add KOH12.3g (0.22mol) under magnetic stirring, cool down in an ice-water bath, and then add 1,5-difluoro-2,4-dinitrobenzene (15g , 73.5mmol) was dissolved in 25mL of tetrahydrofuran, and the solution was placed in a constant pressure dropping funnel and slowly added dropwise to the reaction kettle, and a clear light yellow system was obtained after dropping. In the post-treatment process, 22 g of 36% HCl was still added dropwise in an ice-water bath. After the dropwise addition, THF was evaporated under reduced pressure, and a large amount of beige solid was precipitated after cooling down. After filtration and drying, 13.6 g of solid was obtained, with a yield of 92% and a purity of 99%.

[0040] Step 2, 5-fluoro-2,4-dinitrophenol (50.5g, 0.25mol), ethyl chloroacetate (33.5g, 0.28mol), ethyl 1,1,1-trichloroacetate (57.4g , 0.3mol), potassium carbonate (1.38g, 10mmol), a mixture of 18-cro...

Embodiment 3

[0042] Same as in Example 1, using NaOH instead of KOH in step 1 to prepare 2-(5-fluoro-2,4-dinitrophenoxy)acetate, the yield rate is 90% and the purity is 98%.

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetate. The preparation method comprises the following steps that: step 1, 2, 4-difluoronitrobenzene is used as a raw material, and is hydrolyzed by a base to form 5-fluoro-2,4-dinitrophenol; step 2, a catalyst A and a catalyst B are added into 5-fluoro-2,4-dinitrophenol and ethyl chloroacetate under the action of additives, and a nucleophilic substitution reaction is carried out to obtain the 2-(5-fluoro-2,4-dinitrophenoxy)acetate; the preparation method has the significant advantages of high yield, simple reaction, easy operation and low production costs.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of 2-(5-fluoro-2,4-dinitrophenoxy) acetate. Background technique [0002] Flumioxazin is mainly used as a post-emergence non-selective herbicide, and soybeans and peanuts have good resistance to it. The herbicide has many advantages such as high efficiency, low toxicity, safety to non-target organisms and less environmental pollution. And as the key intermediate of flufenazin propargyl--6-amino-7-fluoro-1,4-benzoxazin-3(4H)-one is generally synthesized using 2-(5-fluoro-2, 4-dinitrophenoxy) acetate is used as a raw material, and the synthetic route has more economical steps, fewer by-products, less waste, and is easy for industrialized production. Therefore, there are many methods around the synthesis of 2-(5-fluoro-2,4-dinitrophenoxy) acetate, such as: [0003] 1. Patent US4640707 discloses m-fluorophenol and ethyl chloroacetate as raw materials...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/37
CPCC07C201/12C07C205/37C07C205/26
Inventor 钱平张璞杨俊施立鑫王凤云陈明光毛更生
Owner 安徽宁亿泰科技有限公司
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