A kind of preparation method of 2,4-difluoro-5-iodobenzoic acid

A technology of iodobenzoic acid and glacial acetic acid, which is applied in two fields, can solve the problems of oxidant waste, difficult iodization reaction, raw material or difficult and expensive reaction, etc., and achieve simple post-processing, good yield and purity, and good yield Effect

Active Publication Date: 2018-08-03
苏州智高嘉华科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there are mainly three types of conventional methods for iodination on the benzene ring in industry. The first type is through the halogen exchange method, and the second type is the diazotization of aniline. There is an activated functional group on the position of the reaction. In this reaction, both the raw materials and the difficulty of the reaction are more expensive than the method of iodination with NIS. The third type is the method of using oxidative iodide, which usually requires a strong Oxidants such as sodium periodate, chromium trioxide, and manganese dioxide, etc., because the third type of reaction is an electrophilic substitution reaction, the iodination reaction is relatively difficult for the electron-deficient benzene ring, and this type of oxidant will produce a large amount of Waste, not a green, atom-economy reaction

Method used

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  • A kind of preparation method of 2,4-difluoro-5-iodobenzoic acid
  • A kind of preparation method of 2,4-difluoro-5-iodobenzoic acid
  • A kind of preparation method of 2,4-difluoro-5-iodobenzoic acid

Examples

Experimental program
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Embodiment 1

[0029] With glacial acetic acid 60ml, I 2 Add 5.33g (21mmol) into a 250ml three-necked flask, and slowly add 4.20g of sodium percarbonate (containing 31mmolH 2 o 2 ), raise the temperature to 35°C under stirring, and add 6.32g (40mmol) of 2,4-difluorobenzoic acid. Cool the reaction solution to 10°C, add 53.30ml of 98% H 2 SO 4 , after the addition, the temperature was raised to 45°C for 2.5 hours, and samples were applied to monitor the end of the reaction. After the reaction, cool the reaction solution, and use potassium iodide starch test paper to detect whether there are oxides in the reaction solution, and if so, use Na 2 SO 3 Aqueous solution (10g sodium sulfite dissolved in 500ml water, the configuration mass fraction is 2% solution) to remove peroxide. Then it was suction filtered and washed once with distilled water to obtain 2,4-difluoro-5-iodobenzoic acid with a yield of 76%. Melting point: 150-153°C.

[0030] Alternatives 1-11

[0031] The preparation metho...

Embodiment 2

[0040] Example 2: Amplified reaction

[0041] With glacial acetic acid 300ml, I 2 Add 26.7g (105mmol) into a 1L three-necked flask, and slowly add 21.0g of sodium percarbonate (SPC) (containing 155mmol H 2 o 2 ), raise the temperature to 35°C under stirring, and add 31.6g (200mmol) of 2,4-difluorobenzoic acid. Cool the reaction solution to 5°C, add dropwise 266.5ml of 98% H 2 SO 4 , after the addition, the temperature was raised to 50°C for 2 hours, and a sample was applied to monitor the end of the reaction. After the reaction, the reaction solution was cooled and washed with 2% Na 2 SO 3 aqueous solution to remove peroxides. Then it was suction filtered and washed to obtain 2,4-difluoro-5-iodobenzoic acid with a yield of 83%.

[0042] In conjunction with embodiment 1-2, and comparative example 1-2, it can be seen that:

[0043] 1. The present invention synthesizes 2,4-difluoro-5-iodobenzoic acid by the iodination reaction under acidic conditions, and iodine reacts ...

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Abstract

The invention discloses a preparation method of 2,4-difluoro-5-iodobenzoic acid. 2,4-difluorobenzoic acid is taken as a starting material, sodium percarbonate and elemental iodine are taken as green iodination reagents, a mild iodination reaction is performed under an acidic condition, and a high-purity target product is obtained. The synthetic process is environment-friendly and suitable for large-scale industrial production, and aftertreatment is convenient.

Description

Technical field: [0001] The invention belongs to the technical field of medicine synthesis, and specifically refers to a preparation method of 2,4-difluoro-5-iodobenzoic acid. Background technique: [0002] AIDS (AIDS) is a fatal disease caused by human immunodeficiency virus (HIV) infection that causes T-cell immune system damage. Up to 60% or more. With the continuous deepening of human research on HIV virus and its infection process, as well as the continuous efforts of drug researchers in various countries, anti-HIV drugs have developed by leaps and bounds, especially the HIV entry inhibitors and HIV integrase inhibitors with new mechanisms of action. It has pointed out a new development direction for the development of anti-HIV drugs and brought new hope for AIDS treatment. [0003] Elvitegravir is a quinolone anti-HIV drug developed by Tobacco Company of Japan and Gilead Sciences Company of the United States. Its trade name is Stribild, and its structural formula is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/363C07C63/70
CPCC07C51/363C07C63/70
Inventor 沈永淼鲁颖颖梁学正李诗恬王丹燕季衡赵欢
Owner 苏州智高嘉华科技有限公司
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