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Preparation method of 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene

A technology of dimethoxybenzene and dimethoxy, which is applied in the field of compound intermediate preparation, can solve the problems of unfriendly environment, high cost of separation and purification, and low yield, so as to avoid column chromatography and achieve high yield , the effect of high product content

Active Publication Date: 2016-07-06
TIANJIN CHENGJIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene is an important intermediate, and there are few reports in the literature at present, Chem.Res.Toxicol.,Vol.12,No. 8,1999 adopts chloroform as a solvent, hydrochloric acid and hydrogen peroxide as a chlorine source, and uses environmentally unfriendly chloroform as a solvent. The reaction is a heterogeneous system, and column chromatography is used to carry out separation and purification. The cost is high, unfriendly to the environment, and the yield is low ( 36%)

Method used

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  • Preparation method of 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene
  • Preparation method of 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add 2.64g of 4-iodo-1,2-dimethoxybenzene and 26ml of acetic acid into a 100ml reaction flask with a tail gas absorption device, then add 30ml of concentrated hydrochloric acid in sequence, and control the temperature of the reaction solution at 15-20 degrees. Slowly add 10ml of hydrogen peroxide diluted with 5ml of glacial acetic acid dropwise. After the dropwise addition, keep stirring at 15-25°C for 12 hours for sampling by HPLC monitoring. If the raw material is less than 1%, add about 30ml of saturated sodium bisulfite solution and filter, transfer the filter cake To a 100ml reaction bottle, add 10ml of acetic acid and 30ml of water, raise the temperature to 50-55°C and stir for 1 hour, then cool down to room temperature and filter with suction, rinse with a little water, TLC test shows a single spot. 3.01 g of white solid were obtained, yield 82%. , HPLC content greater than 97.8%.

Embodiment 2

[0023] Add 1.32g of 4-iodo-1,2-dimethoxybenzene and 6ml of formic acid and 6ml of propionic acid in a 100ml reaction flask with a tail gas absorption device, then add 15ml of concentrated hydrochloric acid in sequence, and control the temperature of the reaction solution for 25 -30°C, slowly add 5ml of hydrogen peroxide diluted with 2.5ml of formic acid dropwise, after the dropwise addition, keep stirring at 25-30°C for 12 hours for sampling by HPLC monitoring, the raw material is less than 1%, add about 15ml of saturated sodium bisulfite solution and filter , transfer the filter cake to a 100ml reaction flask, add 5ml of formic acid and 20ml of water, heat up to 50-60°C and stir for 5 hours, drop to room temperature and suction filter, rinse with a little water, TLC test shows a single spot. 1.46 g of white solid was obtained, yield 80%. HPLC content greater than 98.1%.

Embodiment 3

[0025] Add 5.28g of 4-iodo-1,2-dimethoxybenzene and 52ml of acetic acid into a 250ml reaction flask with a tail gas absorption device, then add 60ml of concentrated hydrochloric acid in sequence, and control the temperature of the reaction solution at 25-35 degrees. Slowly add 20ml of hydrogen peroxide diluted with 10ml of propionic acid dropwise. After the dropwise addition, keep stirring at 25-35°C for 12 hours for sampling by HPLC monitoring. If the raw material is less than 1%, add about 60ml of saturated sodium bisulfite solution and filter, transfer the filter cake To a 250ml reaction bottle, add 20ml of propionic acid and 100ml of water, raise the temperature to 50-55 degrees and stir for 3 hours, then cool down to room temperature and filter with suction, rinse with a little water, TLC test shows a single spot. 5.75 g of white solid was obtained, yield 80.5%. HPLC content greater than 97.9%.

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Abstract

The invention discloses a preparation method of 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene.The preparation method comprises the steps that chlorination is performed by taking 4-iodo-1,2-dimethoxybenzene as a raw material, taking low-carbon-chain fatty acid as solvent and taking hydrogen peroxide and hydrochloric acid or chlorine as a chlorine source, an excessive amount of free chlorine is destroyed by a hydrosulphite solution after reacting is completed, suction filtration, washing under thermal stirring, suction filtration and drying are performed, and then the product with the purity higher than 97% is obtained.TLC shows that the product is a single spot, and HPLC shows that the content is higher than 97%.According to the preparation method of 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene, column chromatography is avoided, operation is simple, and the yield and the purity are high.

Description

technical field [0001] The invention relates to a preparation method of a compound intermediate, in particular to a preparation method of 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene. Background technique [0002] 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene is an important intermediate, and there are few reports in the literature at present, Chem.Res.Toxicol.,Vol.12,No. 8,1999 adopts chloroform as a solvent, hydrochloric acid and hydrogen peroxide as a chlorine source, and uses environmentally unfriendly chloroform as a solvent. The reaction is a heterogeneous system, and column chromatography is used to carry out separation and purification. The cost is high, unfriendly to the environment, and the yield is low ( 36%). Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a preparation method of 1,2-dimethoxy-4-iodobenzene-3,5,6-trichlorobenzene which can overcome the above-mentioned shortcomings of the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/22C07C43/225
CPCC07C41/22C07C43/225
Inventor 谷迎春费学宁林大勇李冉焦秀梅
Owner TIANJIN CHENGJIAN UNIV
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