Green and efficient benzothiophene compound electrochemical synthesis method

A benzothiophene and synthesis method technology, applied in the field of electrochemical synthesis of benzothiophene compounds, can solve problems such as transition metal residues, poor selectivity, and difficult industrial scale-up, and achieve moderate reaction temperature, simple operation, and short reaction time short effect

Pending Publication Date: 2022-05-06
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Purpose of the invention: In order to solve the problems of high cost, residual transition metals, poor selectivity and difficulty in industrial scale-up in the prior art, the present invention provides a green and efficient electrochemical synthesis method of benzothiophene compounds

Method used

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  • Green and efficient benzothiophene compound electrochemical synthesis method
  • Green and efficient benzothiophene compound electrochemical synthesis method
  • Green and efficient benzothiophene compound electrochemical synthesis method

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Embodiment 1

[0033] In a 50mL glass bottle equipped with an electrode, add o-methylthiophenylboronic acid (0.5mmol, 84.02mg), phenylacetylene (1.0mmol, 102.05mg), electrolyte tetrabutylammonium tetrafluoroborate (0.25mmol, 82.32mg) in turn ) and the reaction solvent acetonitrile (9mL) / acetic acid (1mL); the graphite rod electrode was used as the anode, the nickel electrode was used as the cathode to be connected to the DC power supply, and the reaction flask was placed in an oil bath at 60°C and stirred for 3 hours at a constant current of 20mA. ; cooled to room temperature, washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain the target product 2-phenyl-benzothiophene with a yield of 96%. 1 H NMR (400MHz, CDCl 3 )δ7.86(d,J=7.7Hz,1H),7.80(d,J=7.1Hz,1H),7.75(d,J=7.0Hz,2H),7.57(s,1H),7.49–7.42( m,2H),7.41–7.30(m,3H). 13 C NMR(100MHz, CDCl3)δ144.30,140.75,139.5...

Embodiment 2

[0035] In a 50mL glass bottle equipped with an electrode, add o-methylthiophenylboronic acid (0.5mmol, 84.02mg), phenylacetylene (0.5mmol, 51.03mg), electrolyte tetrabutylammonium tetrafluoroborate (0.25mmol, 82.32mg) in turn ) and the reaction solvent acetonitrile (9mL) / acetic acid (1mL); the graphite rod electrode was used as the anode, the nickel electrode was used as the cathode to be connected to the DC power supply, and the reaction flask was placed in an oil bath at 60°C and stirred for 3 hours at a constant current of 20mA. ; cooled to room temperature, washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain the target product 2-phenyl-benzothiophene with a yield of 81%.

Embodiment 3

[0037] In a 50mL glass bottle equipped with an electrode, add o-methylthiophenylboronic acid (0.5mmol, 84.02mg), phenylacetylene (1.5mmol, 153.08mg), electrolyte tetrabutylammonium tetrafluoroborate (0.25mmol, 82.32mg) in turn ) and the reaction solvent acetonitrile (9mL) / acetic acid (1mL); the graphite rod electrode was used as the anode, the nickel electrode was used as the cathode to be connected to the DC power supply, and the reaction flask was placed in an oil bath at 60°C and stirred for 3 hours at a constant current of 20mA. ; cooled to room temperature, washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain the target product 2-phenyl-benzothiophene with a yield of 96%.

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Abstract

The invention discloses a green and efficient benzothiophene compound electrochemical synthesis method which comprises the following steps: adding o-methylthio phenylboronic acid, a phenylacetylene compound and an electrolyte into a reaction solvent, inserting an electrode, and stirring and reacting under constant current to obtain a benzothiophene compound, wherein R is selected from H, C1-C3 alkyl or halogen. According to the method, the benzothiophene is obtained through free radical addition cyclization by utilizing green electrochemical oxidation without participation of a transition metal catalyst and an exogenous strong oxidant, the operation is simple, the cost is low, the reaction is green and efficient, and good guidance is provided for development and application of a benzothiophene-containing drug structure.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a green and efficient electrochemical synthesis method for benzothiophene compounds. Background technique [0002] Benzothiophenes are an important class of structural elements of drugs, natural products, dyes and functional materials. In particular, they are widely present in natural products and synthetic drugs, and have various pharmacological effects such as antimicrobial agents, anticancer agents, anti-inflammatory agents, antioxidants, antituberculosis agents, antidiabetic agents, and anticonvulsants. Due to the important value of these compounds, their synthesis research has always been the focus of organic synthesis. In recent years, the synthesis of benzothiophenes has mostly relied on the assistance of transition metal catalysts. However, due to the problem of metal residues, such methods are used in Applications in the pharmaceutical industry are limited. [0003] I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/05C25B3/11C25B3/23C25B3/29
CPCC25B3/05C25B3/11C25B3/23C25B3/29
Inventor 乔凯张东方正李玉光季栋沈磊郭凯
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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