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The synthetic method of 2‑(5‑fluoro‑2,4‑dinitrophenoxy) acetate

A technology of dinitrophenoxy and a synthesis method, applied in the field of 2-acetate synthesis, can solve problems such as high production cost, difficult separation and purification, and achieve the effects of less side reactions, good selectivity, and easy availability of raw materials

Active Publication Date: 2017-07-07
LIER CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is that the separation and purification of the product is difficult and the production cost is high

Method used

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  • The synthetic method of 2‑(5‑fluoro‑2,4‑dinitrophenoxy) acetate
  • The synthetic method of 2‑(5‑fluoro‑2,4‑dinitrophenoxy) acetate
  • The synthetic method of 2‑(5‑fluoro‑2,4‑dinitrophenoxy) acetate

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preparation example Construction

[0024] The synthetic method of 2-(5-fluoro-2,4-dinitrophenoxy) acetate comprises the following steps:

[0025] a, 2,4-difluoronitrobenzene reacts with glycolate under the action of an acid-binding agent to obtain 2-(5-fluoro-2-nitrophenoxy) acetate and 2-(3-fluoro - a mixture of 4-nitrophenoxy) acetate; the reaction temperature is 40-120°C, and the reaction time is 5-20h; the amount of 2,4-difluoronitrobenzene and glycolic acid ester The ratio is 1:1-1.2; the ratio of the amount of 2,4-difluoronitrobenzene to the acid-binding agent is 1:1-2.5;

[0026] b. React the mixture obtained in step a with nitric acid to obtain 2-(5-fluoro-2,4-dinitrophenoxy)acetate; the reaction temperature is -10°C to 10°C, and the reaction time is 30min ~2h; the ratio of the mixture to the amount of nitric acid is 1:1~1.2.

[0027] In the above-mentioned synthetic method of 2-(5-fluoro-2,4-dinitrophenoxy) acetate, the general formula of the glycolic acid ester described in step a is CH 2 (OH)COOR,...

Embodiment 1

[0031] Example 1 Synthesis of 2-(5-fluoro-2,4-dinitrophenoxy)methyl acetate

[0032] Add 2,4-difluoronitrobenzene (20.4g, 0.1mol), anhydrous potassium carbonate (20.73g, 0.15mol), tetrahydrofuran 102g into the 500mL reaction flask, heat to reflux and slowly drop into methyl glycolate (10.42 g, 0.115mol). After the dropwise addition, continue to reflux for 6 hours, filter and concentrate to obtain methyl 2-(5-fluoro-2-nitrophenoxy)acetate (85%), methyl 2-(3-fluoro-4-nitrophenoxy)acetate (12%) mixture, with a total weight of 22.8g and a yield of 99.5%, was directly used in the next reaction.

[0033] Add 2-(5-fluoro-2-nitrophenoxy)methyl acetate, a mixture of 2-(3-fluoro-4-nitrophenoxy)methyl acetate (22.9g, 0.1mol) into the 500mL reaction flask , 91.6g of dichloroethane, 22.9g of concentrated sulfuric acid, cooled to 0-5°C and slowly added fuming nitric acid (6.3g, 0.1mol) dropwise and continued to react for 30 minutes, separated phases, continued to use dichloroethane Extra...

Embodiment 2

[0035] Example 2 Synthesis of 2-(5-fluoro-2,4-dinitrophenoxy) ethyl acetate

[0036] The methyl glycolate in example 1 is replaced with ethyl glycolate (11.96g, 0.115mol), and the same steps as in Example 1 are adopted to obtain 2-(5-fluoro-2-nitrophenoxy) ethyl acetate A mixture of ester (88%) and ethyl 2-(3-fluoro-4-nitrophenoxy)acetate (10%), total weight 24g, yield 98.4%. Then the mixture was nitrated to finally obtain 26.4 g of solid ethyl 2-(5-fluoro-2,4-dinitrophenoxy)acetate, with a content of 95% and a yield of 91.2%.

[0037] After recrystallization with ethanol, a pure product with a content greater than 98% was obtained, mp: 58.8-59.3°C.

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Abstract

The invention belongs to the field of chemical synthesis, in particular to a synthesis method of 2-(5-fluoro-2,4-dinitrophenoxy) acetate. The technical problem to be solved by the invention is that the separation and purification of the product is difficult and the production cost is high. The scheme of the present invention to solve the above-mentioned technical problems is to provide a kind of synthetic method of 2-(5-fluoro-2,4-dinitrophenoxy) acetate, comprising the following steps: a, 2,4-difluoronitrophenoxy Benzene reacts with glycolate under the action of an acid-binding agent to obtain 2‑(5‑fluoro‑2‑nitrophenoxy) acetate and 2‑(3‑fluoro‑4‑nitrophenoxy) acetic acid A mixture of esters; b, reacting the mixture obtained in step a with nitric acid to obtain 2-(5-fluoro-2,4-dinitrophenoxy) acetate. The invention provides cheap and easy-to-obtain raw materials for the synthesis method, good reaction selectivity, less side reactions, high product yield, mild reaction conditions and easy control, simple process operation and easy industrialization.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a synthesis method of 2-(5-fluoro-2,4-dinitrophenoxy) acetate. Background technique [0002] 2-(5-fluoro-2,4-dinitrophenoxy)acetate is a very useful chemical intermediate, which can be further closed to obtain benzoxazinones, which are used as herbicides The purposes of have been disclosed by patent US4640707 etc. [0003] At present, the methods for synthesizing 2-(5-fluoro-2,4-dinitrophenoxy)acetate mainly include: [0004] 1. Patent US4640707 discloses a method for synthesizing target compounds by etherification and nitration using m-fluorophenol as a raw material. Although this method has high selectivity and few by-products, the starting material m-fluorophenol is expensive and difficult to purchase. [0005] [0006] 2. Patent Laid-open No. 7-48321 and US4803270 disclose a method for synthesizing target compounds by using m-dichlorobenzene as a raw material through st...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/08C07C205/37
Inventor 任杰晏三军李建伟
Owner LIER CHEM CO LTD
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