Asymmetric synthesis method of 4,7-dibromo-2,1,3-diazosulfide symmetric structure

A technology of benzothiadiazole and synthesis method, applied in the direction of organic chemistry, can solve the problems of long reaction time and low reaction yield, achieve the effects of good substrate compatibility, reduce reaction time, and increase conversion rate

Inactive Publication Date: 2018-04-27
GUILIN UNIVERSITY OF TECHNOLOGY
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the Suziki reaction is applied to the asymmetric synthesis of the symmetrical structure of 4,7-dibromo-2,1,3-benzothiadiazole, the reaction system usually use...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Asymmetric synthesis method of 4,7-dibromo-2,1,3-diazosulfide symmetric structure
  • Asymmetric synthesis method of 4,7-dibromo-2,1,3-diazosulfide symmetric structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Analytical pure tetrahydrofuran (THF) and H 2 O is mixed in a volume ratio of 2:1.

[0019] (2) Measure 100 mL of the product obtained in step (1) into a two-necked flask, heat to boiling, and cool to room temperature.

[0020] (3) Weigh 1.617g (5.5mmoL) 4,7-dibromo-2,1,3-benzothiadiazole, 0.7800g (5mmoL) 5-formyl-2-thiophene boronic acid, 1.47g (40mmoL) Potassium carbonate was added to the product obtained in step (2) and stirred for dissolution, under argon protection.

[0021] (4) adding 0.25g mass percent concentration in the product obtained in step (3) is 5% Pd (PPh 3 ) 4 and 0.05mL of analytically pure trioctylmethylammonium chloride, reflux at 90°C, track the reaction with thin-layer chromatography until the concentration of the reactant is basically unchanged, and stop the reaction.

[0022] (5) post-treatment: cooling in the product obtained in step (4), spin-dried, dissolved with analytically pure dichloromethane (DCM), washed with water, extracted, c...

Embodiment 2

[0024] (1) Analytical pure tetrahydrofuran (THF) and H 2 O is mixed in a volume ratio of 2:1.

[0025] (2) Measure 100 mL of the product obtained in step (1) into a 250 mL two-neck flask, heat to boiling, and cool to room temperature.

[0026] (3) Weigh 1.617g (5.5mmoL) 4,7-dibromo-2,1,3-benzothiadiazole, 0.7800g (5mmoL) 5-formyl-2-thiophene boronic acid and 1.47g (40mmoL) Potassium carbonate was added to the product obtained in step (2) and stirred for dissolution, under argon protection.

[0027] (4) adding 0.2042g mass percent concentration in the product obtained in step (3) is 5% Pd(dppf)Cl 2 , reflux at 90°C, track the reaction with thin-layer chromatography until the concentration of the reactant is basically unchanged, and stop the reaction.

[0028] (5) Aftertreatment: the product gained in step (4) is cooled, spin-dried, dissolved with analytically pure dichloromethane (DCM), washed with water, extracted, and the organic phase is collected, spin-dried, and separat...

Embodiment 3

[0030] (1) Analytical pure tetrahydrofuran (THF) and H 2 O is mixed in a volume ratio of 2:1.

[0031] (2) Measure 100 mL of the product obtained in step (1) into a 250 mL two-neck flask, heat to boiling, and cool to room temperature.

[0032] (3) Weigh 1.617g (5.5mmoL) 4,7-dibromo-2,1,3-benzothiadiazole, 0.7800g (5mmoL) 5-formyl-2-thiophene boronic acid and 1.47g (40mmoL) Potassium carbonate was added to the product obtained in step (2) and stirred for dissolution, under argon protection.

[0033] (4) adding 0.2042g mass percent concentration in the product obtained in step (3) is 5% Pd(dppf)Cl 2 and 0.05mL of analytically pure trioctylmethylammonium chloride, reflux at 90°C, track the reaction with thin-layer chromatography until the concentration of the reactant is basically unchanged, and stop the reaction.

[0034] (5) post-processing: the product obtained in step (4) is cooled, spin-dried, dissolved with analytically pure dichloromethane (DCM), washed with water, extr...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses an asymmetric synthesis method of a 4,7-dibromo-2,1,3-diazosulfide symmetric structure. The purpose of optimizing conditions of coupling reaction of 4,7-dibromo-2,1,3- diazosulfide C-C coupling reaction is achieved, on the basis of Suziki reaction, THF/H2O is used as a solvent system, Pd(PPh3)4 or Pd(dppf)Cl2 is used as a palladium catalyst, a phase transfer catalyst whichis methyl trioctyl ammonium chloride and the like is introduced, reaction conditions are mild, moreover, the reaction time is shortened, and the percent conversion of a reactant is increased. The synthesis method is simple to operate, the compatibility of a substrate is good, and therefore, the method can be applied to synthesis of organic compounds with similar structures well.

Description

technical field [0001] The invention relates to an asymmetric synthesis method of an organic substance with a symmetrical structure, which aims at optimizing the conditions of the C-C coupling reaction of 4,7-dibromo-2,1,3-benzothiadiazole, and belongs to the field of organic chemical synthesis. Background technique [0002] Benzothiadiazole compounds are a class of compounds containing nitrogen and sulfur heterocycles. Due to their strong electron affinity, co-planarity and good adjustability to the energy level of the compound, they are widely used in Construction of conjugated organic molecules. In recent years, there have been more and more studies on benzothiadiazole and its derivatives, which have been applied to organic light-emitting diodes, dye intermediates, OLEDs, medicine, etc. (Fang Shaoming, Su Jigong, Wang Guohao, etc. 4 ,6-2,1,3-Benzothiadiazole: a new building block and multi-performance regulator of polymer optoelectronic functional materials[J].Organic Ch...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D417/04
CPCC07D417/04
Inventor 谭海军裴海睿何敬文
Owner GUILIN UNIVERSITY OF TECHNOLOGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap