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Trifluoromethyl substituted benzofuran derivatives and preparation method thereof

A technology of benzofuran and trifluoromethyl, which is applied in the field of trifluoromethyl-substituted benzofuran derivatives and its preparation, can solve problems such as poor yield and selectivity, harsh reaction conditions, and few synthetic studies , to achieve high yield, mild synthesis conditions and simple synthesis steps

Inactive Publication Date: 2008-09-17
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic research of the benzofuran compound of trifluoromethyl modification is relatively few, and in their synthetic method, some use trifluoroiodomethane gas (J.Chem.Soc.PerkinTrans.I., 1980,661) , productive rate and selectivity are bad; Some use trifluoropropyne gas (Bull Chem.Soc.Jpn., 1990,63,2124), harsh reaction conditions; Some use expensive palladium catalyst (J.Fluorine Chem ., 2003, 123, 57; Tetrahedron, 2004, 60, 11695), the cost is higher

Method used

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  • Trifluoromethyl substituted benzofuran derivatives and preparation method thereof
  • Trifluoromethyl substituted benzofuran derivatives and preparation method thereof
  • Trifluoromethyl substituted benzofuran derivatives and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0020] The general structural formula is I, wherein, R 1 , R 2 , R 3 Preparation of the benzofuran derivative of H, 2-trifluoromethylbenzofuran.

[0021] Dissolve 1 mL of the compound salicylaldehyde in 10 mL of N,N-dimethylformamide, under nitrogen balloon protection, at room temperature, add 3.25 g of zinc powder, 2.8 mL of acetic anhydride, stir, and dropwise add 1, 1,1-Trichloro-2,2,2-Trifluoroethane 3.6mL, after dropwise addition, continue to react for 3 hours, add 50mL saturated ammonium chloride solution and 50mL ethyl acetate, separate liquid, extract with ethyl acetate The aqueous layer was collected and the organic phase was concentrated to obtain a dark brown liquid, which was separated and purified by flash column chromatography using petroleum ether as an eluent to obtain 1.32 g of a light brown liquid with a yield of 50%. Dissolve this compound in 5mL of N,N-dimethylformamide, add 1.68g of potassium tert-butoxide at room temperature, react for 3 hours, add 25m...

Embodiment 2

[0024] The general structural formula is I, wherein, R 1 for CH 3 , R 2 , R 3 Preparation of the benzofuran derivative 5-methyl-2-trifluoromethylbenzofuran as H.

[0025] Dissolve 1.36g of the compound 5-methyl salicylaldehyde in 10mL of N,N-dimethylformamide, under nitrogen balloon protection, at room temperature, add 3.25g of zinc powder, 3.0mL of acetic anhydride, stir, and add Add dropwise 3.6mL of 1,1,1-trichloro-2,2,2-trifluoroethane, after the dropwise addition, react for 3 hours, add 50mL of saturated ammonium chloride solution and 50mL of ethyl acetate, separate liquid, acetic acid The aqueous layer was extracted with ethyl ester, the organic phase was collected and concentrated, and the resulting brown liquid was separated and purified by flash column chromatography using petroleum ether as an eluent to obtain 1.25 g of a light brown liquid with a yield of 45%. Dissolve this compound in 5mL of N,N-dimethylformamide, add 1.57g of potassium tert-butoxide at room te...

Embodiment 3

[0028] The general structural formula is I, wherein, R 1 for Cl, R 2 , R 3 Preparation of the benzofuran derivative of H, 2-trifluoromethyl-5-chlorobenzofuran.

[0029] Dissolve 1.57g of the compound 5-chlorosalicylaldehyde in 10mL of N,N-dimethylformamide, under nitrogen balloon protection, at room temperature, add 3.51g of zinc powder, 3.7mL of acetic anhydride, stir, and dropwise add 1,1,1-Trichloro-2,2,2-Trifluoroethane 4.0mL, after the dropwise addition, react for 4 hours, add 50mL saturated ammonium chloride solution and 50mL ethyl acetate, separate liquid, ethyl acetate The aqueous layer was extracted, the organic phase was collected and concentrated, and the obtained brown liquid was separated and purified by flash column chromatography using petroleum ether as an eluent to obtain 1.31 g of a light yellow solid with a yield of 44%. Dissolve this compound in 5mL of N,N-dimethylformamide, add 1.48g of potassium tert-butoxide at room temperature, react for 3 hours, add...

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Abstract

The invention relates to 2-(substituted trifluoromethyl) benzofuran derivatives, and a preparation method thereof, in particular to derivative in the formula, wherein R<1> is selected from H, CH3, Cl, Br, C(CH3)3, OH, CH3CO or COOC2H5; R<2> is selected from H or OH; and R<3> is selected from H, Cl, C(CH3)3 or OCH3. The trifluoromethyl modified benzofuran compounds synthesized by the invention contain a plurality of functional groups in benzene ring portion, and can be used as precursor for subsequent synthesis of benzofuran medicine intermediate containing trifluoromethyl. The method for synthesizing 2-(substituted trifluoromethyl) benzofuran derivatives has easily available raw material, simple process, easy realization and high yield.

Description

technical field [0001] The present invention relates to trifluoromethyl-substituted benzofuran derivatives and a preparation method thereof. technical background [0002] Benzofuran derivatives widely exist in nature, and many natural products contain benzofuran derivatives, many of which are biologically active compounds, and many of them have important medicinal value. The physiological activities of benzofuran derivatives that have been discovered include insecticide, antibacterial, antimicrobial and anti-oxidation, etc. In recent years, research on benzofuran derivatives in antiviral, antitumor, and nervous system regulation has also gained important Progress. Benzofuran derivatives have attracted extensive attention due to their remarkable biological activities, and many methods for the synthesis of such compounds have been established. Trifluoromethyl has a unique position in drug design. After introducing trifluoromethyl into organic molecules, the lipid solubility ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79
Inventor 徐经伟周华牛佳佳李志刚
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI