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Synthetic method of 5-trifluoromethyl pyrrole-2-formic acid

A technique for the synthesis of trifluoromethylpyrrole, which is applied in organic chemistry and other fields, can solve the problems of difficulty in purification and low yield of synthetic routes, and achieve the effect of easy purification and high yield

Active Publication Date: 2012-12-19
SHANGHAI STA PHARMA R&D CO LTD
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  • Description
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Problems solved by technology

[0007] The purpose of the present invention is to provide a new synthetic method of 5-trifluoromethylpyrrole-2-carboxylic acid, which mainly solves the technical problems of low yield and difficult purification of existing synthetic routes

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  • Synthetic method of 5-trifluoromethyl pyrrole-2-formic acid

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Embodiment 1

[0018] Methyl pyrrole-2-carboxylate (1 g, 8 mmol) and sodium trifluorosulfinate (5 g, 32 mmol) were dissolved in a mixed solution (10 mL) of dichloromethane and water in a volume ratio of 2:1 , Peroxy tert-butanol (8 g, 64 mmol) was added dropwise to the reaction solution at room temperature for 24 hours. Saturated sodium sulfite solution was quenched with tert-butanol peroxy, extracted with dichloromethane (200 mL*2), the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent, and the filtrate was concentrated and chromatographed on silica gel Column purification gave methyl 5-trifluoromethylpyrrole-2-carboxylate (0.5 g, 32.5% yield).

[0019] H NMR spectroscopy (CDCl 3, 400 MHz), δ ppm: 3.86 (s, 3H); 6.57-6.60 (m, 1H); 6.85-6.88 (m, 1H); 10.10 (s, 1H).

Embodiment 2

[0021] Methyl pyrrole-2-carboxylate (5 g, 40 mmol) and sodium trifluorosulfinate (25 g, 160 mmol) were dissolved in a mixed solution (50 mL) of dichloromethane and water in a volume ratio of 2:1 , Peroxy tert-butanol (40 g, 320 mmol) was added dropwise to the reaction solution at room temperature for 30 hours. Saturated sodium sulfite solution was quenched with tert-butanol peroxy, extracted with dichloromethane (500 mL*2), the organic phases were combined and washed with saturated brine, anhydrous Na 2 SO 4 After drying, the desiccant was removed by filtration, and the filtrate was concentrated and purified by silica gel column chromatography to obtain methyl 5-trifluoromethylpyrrole-2-carboxylate (2.7 g, yield 34.97%).

Embodiment 3

[0023] Methyl pyrrole-2-carboxylate (35 g, 0.28 mol) and sodium trifluorosulfinate (175 g, 1.12 mol) were dissolved in a mixed solution (300 mL) of dichloromethane and water with a volume ratio of 2:1 , and tert-butanol peroxy (280 g, 2.24 mol) was added dropwise to the reaction solution at room temperature for 36 hours. Saturated sodium sulfite solution was quenched with tert-butanol peroxy, extracted with dichloromethane (1 L*2), the combined organic phases were washed with saturated brine, anhydrous Na 2 SO 4 After drying, the desiccant was removed by filtration, and the filtrate was concentrated, and purified by silica gel column chromatography to obtain methyl 5-trifluoromethylpyrrole-2-carboxylate (19 g, yield 35.19%).

[0024] 2 . Synthesis of 5-trifluoromethylpyrrole-2-carboxylic acid

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Abstract

The invention relates to a novel synthetic method of 5-trifluoromethyl pyrrole-2-formic acid, which mainly solves the technical problems that the current synthetic method has low yield and is difficult to realize purification. The technical scheme is that the synthetic method of 5-trifluoromethyl pyrrole-2-formic acid comprises the following steps of: 1, taking pyrrole-2-methyl formate as a raw material; using dichloromethane and water mixing solution as a solvent to synthesize 5-trifluoromethyl pyrrole-2-methyl formate in presence of sodium trifluorosulfinate; and 2, reflowing the 5-trifluoromethyl pyrrole-2-methyl formate through acetonitrile in presence of trimethylchlorosilane and sodium iodide, so as to obtain a target product 5-trifluoromethyl pyrrole-2-formic acid. The compound obtained in the method provided by the invention is mainly served as an intermediate for further synthesizing.

Description

technical field [0001] The invention relates to a method for synthesizing 5-trifluoromethylpyrrole-2-carboxylic acid, a fluorine-containing organic synthesis intermediate. Background technique [0002] The atomic radius of fluorine is small, and it has greater electronegativity, so the C-F bond energy it forms is much larger than the C-H bond energy, which significantly increases the stability and physiological activity of organic fluorine compounds. Fluorine-containing organic compounds also have high fat solubility and hydrophobicity, thereby increasing the penetration ability of membranes and tissues in living organisms, promoting their absorption and delivery speed in living organisms, and changing physiological functions. Therefore, many fluorine-containing medicines and pesticides have the characteristics of less dosage, low toxicity, high efficacy and strong metabolism in terms of performance. Therefore, the introduction of fluorine atoms into organic molecules and t...

Claims

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Application Information

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IPC IPC(8): C07D207/34
Inventor 王帅黄凤莺张歆宁柏祝董径超
Owner SHANGHAI STA PHARMA R&D CO LTD
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