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Novel synthesis method of benzene ring polysubstituted compound based on benzoyl formic acid

A technology of benzoylformic acid and a synthesis method, applied in the field of organic compound synthesis, can solve the problems of lack of safety and efficiency, low toxicity, high reaction temperature, high pyridine toxicity, etc., and achieve the effects of easy operation, high yield and easy reaction

Active Publication Date: 2020-05-08
苏州爱玛特生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, if selenium dioxide is used as an oxidant, the elemental selenium obtained after selenium dioxide is reduced will become an environmental pollutant.
Using pyridine as a solvent, due to the high toxicity of pyridine, high reaction temperature, difficult operation, low safety and low yield
Therefore, at present, there is still a lack of safe, efficient, and low-toxicity synthetic methods

Method used

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  • Novel synthesis method of benzene ring polysubstituted compound based on benzoyl formic acid
  • Novel synthesis method of benzene ring polysubstituted compound based on benzoyl formic acid
  • Novel synthesis method of benzene ring polysubstituted compound based on benzoyl formic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] This embodiment provides the synthesis of 2-(2-chlorobenzene)-2-glyoxylic acid, and the synthetic route is as follows:

[0029]

[0030] The specific synthesis method is: add 1-(2-chlorobenzene)ethan-1-one (0.15g, 1.0mmol) and 50mL trifluorotoluene in a flask, stir to make 1-(2-chlorobenzene)ethan-1-one Dissolve in trifluorotoluene, add 2N HCl (0.5mL), then add sodium dichromate (0.30g, 2.0mmol) under acidic conditions, heat to 95°C and reflux at this temperature for 6h. After the reaction is over, remove the trifluorotoluene in the system, add sodium hydroxide to the water phase to adjust the pH of the water phase to 9 to remove impurities, then add hydrochloric acid to the water phase to adjust the pH of the water phase to 3, extract, The product 2-(2-chlorobenzene)-2-glyoxylic acid (0.17 g) was obtained by recrystallization from petroleum ether, with a yield of 90%.

[0031] Carry out nuclear magnetic detection to product, the result is:

[0032] 1 H NMR (400MH...

Embodiment 2

[0035] This example provides the synthesis of 2-(2-fluorobenzene)-2-glyoxylic acid

[0036]

[0037] The specific synthetic operation method is the same as in Example 1, specifically: add 1-(2-fluorobenzene) ethyl-1-ketone (1mmol) and 50mL trifluorotoluene into a flask, and stir to make 1-(2-fluorobenzene) ethyl alcohol -1-Kone was dissolved in trifluorotoluene, then 2N HCl (0.5mL) was added, and then sodium dichromate (0.30g) was added under acidic conditions, heated to 95°C and refluxed at this temperature for 6h. After the reaction is over, remove the benzotrifluoride in the system, add sodium hydroxide to the water phase to adjust the pH to 9 to remove impurities, then add hydrochloric acid to the water phase to adjust the pH to 3, extract, The product 2-(2-fluorobenzene)-2-glyoxylic acid was obtained by recrystallization from petroleum ether with a yield of 88%.

[0038] Carry out nuclear magnetic detection to product, the result is:

[0039] 1 H NMR (400MHz, CDCl3)...

Embodiment 3

[0042] This embodiment provides the synthesis of 2-(2-bromobenzene)-2-glyoxylic acid

[0043]

[0044] The specific synthetic operation method is the same as in Example 1, specifically: add 1-(2-bromobenzene) ethyl-1-ketone (1mmol) and 50mL trifluorotoluene in a flask, and stir to make 1-(2-bromobenzene) ethyl alcohol -1-Kone was dissolved in trifluorotoluene, then 2N HCl (0.5mL) was added, and then sodium dichromate (0.30g) was added under acidic conditions, heated to 95°C and refluxed at this temperature for 6h. After the reaction is over, remove the trifluorotoluene in the system, add sodium hydroxide to the water phase to adjust the pH of the water phase to 9 to remove impurities, then add hydrochloric acid to the water phase to adjust the pH of the water phase to 3, extract, The product 2-(2-bromobenzene)-2-glyoxylic acid was obtained by recrystallization from petroleum ether with a yield of 90%.

[0045] Carry out nuclear magnetic detection to product, the result is: ...

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Abstract

The invention relates to a novel synthesis method of a benzene ring polysubstituted compound based on benzoyl formic acid. According to the synthesis method, an acetophenone-based benzene ring polysubstituted compound is used as a raw material, a specific oxidant dichromate is used as an oxidant, and an oxidation reaction is carried out in the presence of an organic solvent and an acidic substanceto prepare the benzoyl formic acid-based benzene ring polysubstituted compound. The synthesis method disclosed by the invention has the advantages of good stability, high safety, easiness in reactionregeneration and high yield, and is milder, low in toxicity, easy to operate and high in efficiency compared with the disclosed synthesis method.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a novel synthesis method of benzoylformic acid-based benzene ring multi-substituted compounds. Background technique [0002] Benzoylformic acid-based benzene ring polysubstituted compounds are an important class of pharmaceutical intermediates and are widely used in the field of medicinal chemistry. [0003] At present, the synthesis method of this type of structure prepared by using acetophenone-based multi-substituted benzene ring compounds as raw materials is relatively simple, and selenium dioxide is generally used as an oxidant and pyridine as a solvent. [0004] For example, references: Beebe X, Nilius A M, Merta P J, et al. Synthesis and SARevaluation of oxadiazolopyrazines as selective Haemophilus influenzae antibacterial agents [J]. Bioorganic & Medicinal Chemistry Letters, 2003, 13(19): 3133-3136. [0005] The specific method in this refe...

Claims

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Application Information

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IPC IPC(8): C07C59/84C07C51/16C07C59/88
CPCC07C51/16C07C59/88C07C59/84Y02P20/55
Inventor 汪明中朱明新苏道李金金
Owner 苏州爱玛特生物科技有限公司