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Perfluoroalkyl pyrrole derivative and synthesis method thereof

A technology of perfluoroalkylpyrrole and perfluoroalkylalkynoate, applied in the field of perfluoroalkylpyrrole derivatives and their synthesis

Active Publication Date: 2015-11-04
SHANGHAI MACKLIN BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Summarizing the synthesis methods so far, it is not difficult to see that in the previous synthesis methods, strong bases or metals were often required as catalysts; or in two steps, but The step-by-step reaction often makes the reaction steps cumbersome and complicates the operation. Both the catalyst and the step-by-step method have their shortcomings.
Furthermore, there are almost no perfluoroalkyl-containing products in the currently synthesized pyrrole derivatives. Therefore, we propose a synthetic method that is atom-economical, environmentally friendly, easy to operate, and readily available raw materials. A series of perfluoroalkylpyrrole derivatives

Method used

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  • Perfluoroalkyl pyrrole derivative and synthesis method thereof
  • Perfluoroalkyl pyrrole derivative and synthesis method thereof
  • Perfluoroalkyl pyrrole derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Add w-bromoacetophenone (99.5 mg, 0.5 mmol), aniline (55.8 mg, 0.6 mmol), sodium bicarbonate (84 mg, 1 mmol) and dimethyl sulfoxide ( 5 mL) as a solvent, reacted at room temperature for 3 hours, then added methyl trifluoromethylynoate (152 mg, 1 mmol), raised the temperature to 100°C and reacted for 8 hours, cooled to room temperature and washed with saturated saline and ethyl acetate The ester was extracted three times, the organic layers were combined and spin-dried, and the pure product was obtained by column chromatography. White transparent liquid. Yield 88%.

[0026] Structural formula:

[0027]

[0028] Chinese name: 1,4-diphenyl-2-(trifluoromethyl)-1 H - Methyl pyrrole-3-carboxylate

[0029] English name: methyl 1,4-diphenyl-2-(trifluoromethyl)-1 H -pyrrole-3-carboxylate

[0030] Molecular weight: 345.10

[0031] Appearance: white transparent liquid

[0032] Proton NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): δ: 3.85 (s, 3H), 6....

example 2

[0035] Example 2: Add p-methyl w-bromoacetophenone (105.5 mg, 0.5 mmol), aniline (55.8 mg, 0.6 mmol), sodium bicarbonate (84 mg, 1 mmol) and dimethylmethylene in a round bottom flask Sulfone (5 mL) was used as solvent, reacted at room temperature for 3 hours, then added methyl trifluoromethyl alkynoate (152 mg, 1 mmol), raised the temperature to 100°C and reacted for 8 hours, cooled to room temperature and washed with saturated saline and Ethyl acetate was extracted three times, the organic layers were combined and spin-dried, and the pure product was obtained by column chromatography. white solid. Yield 88%.

[0036] Structural formula:

[0037]

[0038] Chinese name: 1-phenyl-4-(p-tolyl)-2-(trifluoromethyl)-1 H - Methyl pyrrole-3-carboxylate

[0039] English name: methyl 1-phenyl-4-( p -tolyl)-2-(trifluoromethyl)-1 H -pyrrole-3-carboxylate

[0040] Molecular weight: 359.11

[0041] Appearance: white solid

[0042] Melting point: 88.7-90.0 °C

[0043] Proton NMR ...

example 3

[0046] Example 3: Add p-methoxyl w-bromoacetophenone (114 mg, 0.5 mmol), aniline (55.8 mg, 0.6 mmol), sodium bicarbonate (84 mg, 1 mmol), dimethyl Sulfoxide (5 mL) was used as solvent, reacted at room temperature for 3 hours, then added methyl trifluoromethyl alkynoate (152 mg, 1 mmol), raised the temperature to 100°C and reacted for 8 hours, cooled to room temperature and washed with saturated saline Extracted with ethyl acetate three times, the organic layer was combined and spin-dried, and separated by column chromatography to obtain a pure product. white solid. Yield 91%.

[0047] Structural formula:

[0048]

[0049] Chinese name: 1-phenyl-4-(p-methoxyphenyl)-2-(trifluoromethyl)-1 H - Methyl pyrrole-3-carboxylate

[0050] English name:

[0051] methyl 1-phenyl-4-(4-methoxyphenyl)-2-(trifluoromethyl)-1 H -pyrrole-3-carboxylate

[0052] Molecular weight: 375.11

[0053] Appearance: white solid

[0054] Melting point: 79.9-80.8 °C

[0055] Proton NMR spectrum (5...

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Abstract

The present invention relates to a perfluoroalkyl pyrrole derivative and a synthesis method thereof, wherein the structure of the compound is defined in the specification, R1 is -H, -CH3, -OCH3, -NO2 or -Cl, R2 is -H, -CH3, -OCH3, -F or -Cl, and RF is -CF3, C2F5, or n-C3F7. According to the present invention, the perfluoroalkyl is firstly introduced into the pyrrole derivative through the method, and a series of compounds with characteristics of novel structure and high regioselectivity are synthesized by using the novel method; and the three-component step-by-step one-pot synthesis method is used, the method has advantages of atom economy, environmental protection, easy operation and mild conditions compared with the previously reported methods, and the product yield is good.

Description

technical field [0001] The invention relates to a perfluoroalkylpyrrole derivative and a synthesis method thereof. Background technique [0002] Pyrrole derivative monomer is an important class of five-membered nitrogen heterocyclic compounds. As an important intermediate of fine chemical products, it has a wide range of applications in the fields of medicine, food, pesticides, daily chemicals, coatings, textiles, and polymer materials. use. Therefore, the synthetic method of this kind of compound is studied extensively by people. [0003] However, how to synthesize rings economically and efficiently is still a hotspot in synthesis. Judging from many published research results, although many pyrroles with different structures have been synthesized, no compounds with perfluoroalkyl groups introduced into them have yet appeared. [0004] Currently reported synthetic methods for the preparation of pyrrole derivatives are listed below: [0005] (1) The most classic method in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 孙雪春韩靖陈杰张慧曹卫国
Owner SHANGHAI MACKLIN BIOCHEM TECH