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A kind of preparation method of 3-nitro-4-fluorophenyl acetate

A technology of fluorophenylacetate and ethyl fluorophenylacetate, which is applied in the field of preparation of 3-nitro-4-fluorophenylacetate, can solve the problems of low conversion rate of raw materials and poor spatial position selectivity, and achieve safety High performance, control the problem of heat release, and avoid the effect of rapid heat dissipation

Active Publication Date: 2022-06-24
暨明医药科技(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is that in the method for preparing 3-nitro-4-fluorophenylacetic acid ester from 4-fluorophenylacetic acid ester in the prior art, there are technologies such as low raw material conversion rate and poor spatial position selectivity. question

Method used

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  • A kind of preparation method of 3-nitro-4-fluorophenyl acetate
  • A kind of preparation method of 3-nitro-4-fluorophenyl acetate
  • A kind of preparation method of 3-nitro-4-fluorophenyl acetate

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Experimental program
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Effect test

Embodiment 1

[0034] (1) Preparation of raw materials: Take 200 g of ethyl 4-fluorophenylacetate and dissolve it in 280 mL of 98% sulfuric acid for later use. Take 79mL of 69% nitric acid for use.

[0035] (2) Pre-cooling: Cool the pre-cooling module and the mixing module to 0-10°C. The sulfuric acid solution and nitric acid solution of ethyl 4-fluorophenylacetate were pumped into two parallel pre-cooling modules with two constant-flow pumps for cooling to 0-10 °C.

[0036] (3) mixing: after the raw material pre-cooling is completed, enter the mixing module for mixing reaction, the flow rate of the mixed solution of ethyl 4-fluorophenylacetate and the vitriol oil is set to 15mL / min, the flow rate of nitric acid is 2.63mL / min, and the reaction stays in the mixing module 42s.

[0037] (4) Quenching and post-treatment: the reaction solution was quenched in a quenching tank, and there were 500 mL of ethyl acetate and 500 mL of water in the quenching tank. The reaction solution was quenched a...

Embodiment 2-9

[0039] The preparation method is the same as in Example 1, and the fixed consumption of ethyl 4-fluorophenylacetate is 200 g, the difference lies in the consumption of raw materials and some process parameters. At the same time, in order to ensure that the mixed solution of 4-fluorophenylacetate and concentrated sulfuric acid and the nitric acid solution entering the mixing module of the microreactor can fully participate in the reaction, the flow rate is also changed as required. The products after the reaction are denoted as S2-S9.

Embodiment 10

[0042] (1) Preparation of raw materials: Take 185 g of methyl 4-fluorophenylacetate and dissolve it in 280 mL of 98% sulfuric acid for later use. Take 79mL of 69% nitric acid for use.

[0043] (2) Pre-cooling: Cool the pre-cooling module and the mixing module to 0-10°C. The sulfuric acid solution and nitric acid solution of methyl 4-fluorophenylacetate were pumped into two parallel pre-cooling modules with two constant-flow pumps for cooling to 0-10 °C.

[0044] (3) mixing: after the pre-cooling of the raw materials is completed, enter the mixing module for mixing reaction, the flow rate of the mixed solution of 4-fluorophenylacetate and the concentrated sulfuric acid is set to 14.8mL / min, the flow rate of nitric acid is 2.63mL / min, and the reaction is carried out in the mixing module. Stay for 42s.

[0045] (4) Quenching and post-treatment: the reaction solution was quenched in a quenching tank, and there were 500 mL of ethyl acetate and 500 mL of water in the quenching tan...

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Abstract

The invention discloses a method for preparing 3-nitro-4-fluorophenylacetate by using a microreactor, which belongs to the technical field of organic compound synthesis, wherein the microreactor includes a precooling module and a mixing module, specifically comprising the following steps: ( 1) Prepare raw materials: prepare a mixed solution of 4-fluorophenyl acetate and concentrated sulfuric acid, and nitric acid solution; (2) pre-cooling: cool down the pre-cooling module and the mixing module to the reaction temperature in advance, and then respectively add 4-fluorophenylethyl The mixed solution of acid ester and concentrated sulfuric acid, and nitric acid solution are added to different pre-cooling modules; (3) Mixing: After the raw materials are pre-cooled, they are added to the mixing module for mixing reaction; (4) Quenching and post-processing. The method of the present invention can effectively control the exothermic problem of nitration reaction, and has high safety; and can prepare 3-nitro-4-fluorophenylacetate with high selectivity, and the conversion rate of 4-fluorophenylacetate can reach 98.4 %, the selectivity can reach 99:1.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of 3-nitro-4-fluorophenyl acetate. Background technique [0002] Dihydronaphthyridines are a class of kinase inhibitors for the treatment or prevention of diseases such as gastrointestinal stromal tumors, acute myeloid leukemia and systemic hypertrophy. In the construction of dihydronaphthyridines, 3-nitro-4-fluorophenylacetate is an important intermediate, but the method for synthesizing 3-nitro-4-fluorophenylacetate is more complicated, and it is not easy to There are literature reports. [0003] The literature (Synthesis of azide-fluoro-dehydrocoelenterazine analog as aphotoaffinity-labeling probe and photolysis of azide-fluoro-coelenterazine. M.Kuse et al. Tetrahedron, 2005, 61, 5754-5762) discloses a 4-fluorobenzene Using ethyl acetate as a raw material, the method for obtaining ethyl 3-nitro-4-fluorophenylacetate through a nitration reaction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/08C07C205/56
CPCC07C201/08C07C205/56
Inventor 陈剑戈李斌峰苑可
Owner 暨明医药科技(苏州)有限公司