Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing substituted alkene

A technology for olefins and halogenated hydrocarbons is applied in the field of catalytic coupling synthesis of substituted olefins to achieve the effects of easy availability of raw materials, simple operation and convenient post-processing

Inactive Publication Date: 2012-10-24
SUZHOU UNIV
View PDF2 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for the traditional Heck reaction, cinnamate derivatives are generally obtained, which has certain limitations for the synthesis of substituted olefin compounds with other functional groups

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
  • Method for preparing substituted alkene
  • Method for preparing substituted alkene
  • Method for preparing substituted alkene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Pd(dppf) was sequentially filled in a Schlenk test tube 2 Cl 2 (0.015 mmol), triethylamine (1.0 mmol), potassium vinylfluoroborate (0.5 mmol) and DMF (2 mL), and iodobenzene (0.5 mmol) was added with a microinjector. Then the system was sealed and heated in an oil bath at 120°C for about 12 hours, then p-methoxyiodobenzene (0.5 mmol) was added, and the system was sealed and heated in an oil bath at 120°C for about 24 hours. The system was then allowed to cool to room temperature, 2 mL of water was added to quench the reaction, and then extracted with ethyl acetate (4 mL×3), the organic phases were combined and dried over anhydrous sodium sulfate, concentrated and passed through simple column chromatography (eluent used Petroleum ether:ethyl acetate=24:1) to obtain the coupling product 1-phenyl 2-p-methoxyphenylethylene (85.2 mg), with a yield of 81%. Its NMR data are: 1 H NMR (400 MHz, CDCl 3 ) (δ, ppm) 3.81 (s, 3H), 6.89 (d, J = 8.4 Hz, 2H), 6.96 (d, J = 16.0 Hz, ...

Embodiment 2

[0034] Pd(dppf) was sequentially filled in a Schlenk test tube 2 Cl 2 (0.015 mmol), triethylamine (1.0 mmol), potassium vinylfluoroborate (0.5 mmol) and DMF (2 mL), and p-chloroiodobenzene (0.5 mmol) was added with a microinjector. Then the system was sealed and heated in an oil bath at 120°C for about 12 hours, then p-fluoroiodobenzene (0.5 mmol) was added, and then the system was sealed and heated in an oil bath at 120°C for about 24 hours. The system was then allowed to cool to room temperature, and 2 mL of water was added to quench the reaction, followed by extraction with ethyl acetate (4 mL × 3), the combined organic phases were dried over anhydrous sodium sulfate, concentrated and passed through simple column chromatography (eluent used Petroleum ether:ethyl acetate=24:1) to obtain the coupling product 1-p-chlorophenyl 2-p-fluorophenylethylene (97.4 mg), with a yield of 84%. Its NMR data are: 1 H NMR (400 MHz CDCl 3) 6.98 (d, J = 16.4, 1H), 7.04-7.09 (m, 3H), 7.35 ...

Embodiment 3

[0036] Pd(dppf) was sequentially filled in a Schlenk test tube 2 Cl 2 (0.015 mmol), triethylamine (1.0 mmol), potassium vinylfluoroborate (0.5 mmol) and DMF (2 mL), and p-fluoroiodobenzene (0.5 mmol) was added with a microinjector. Then the system was sealed and heated in an oil bath at 120°C for about 12 hours, then p-methoxyiodobenzene (0.5 mmol) was added, and the system was sealed and heated in an oil bath at 120°C for about 24 hours. The system was then allowed to cool to room temperature, 2 mL of water was added to quench the reaction, and then extracted with ethyl acetate (4 mL×3), the organic phases were combined and dried over anhydrous sodium sulfate, concentrated and passed through simple column chromatography (eluent used Petroleum ether:ethyl acetate=24:1) to obtain the coupling product 1-p-methoxyphenyl 2-p-fluorophenylethylene (92.4 mg), with a yield of 81%. Its NMR data are: 1 H NMR (400 MHz CDCl 3 ) 3.84 (s, 3H), 6.84-6.96 (m, 4H), 7.03 (t, J = 8.8, 2H), ...

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 a method for preparing substituted alkene. The method is characterized in that Suzuki coupling reaction and Heck coupling reaction occur in turn under the action of a catalyst with a vinyl fluoride potassium silicate compound and halogenated hydrocarbon as a reaction substrate to obtain the substituted alkene, wherein the halogenated hydrocarbon is a halogenated aromatic hydrocarbon or a halogenated aliphatic hydrocarbon, the halogen atom is selected from chlorine, bromine or iodine; the vinyl fluoride potassium silicate compound refers to an olefin compound with double bond connected with boric acid group, the catalyst is a palladium catalyst. The method provided by the invention has the advantages of simple operation, mild condition, convenient post-processing, easiness of geting raw materials and wide range of suitable substrates.

Description

technical field [0001] The invention relates to the preparation of a substituted olefin, in particular to a method for catalytically coupling and synthesizing a substituted olefin, in particular to a method for preparing a substituted olefin through a series reaction of Suzuki coupling and Heck coupling. Background technique [0002] Substituted alkene structural units widely exist in the intermediates of medicine and materials, and their effective synthesis methods have attracted widespread attention in the past decade. Therefore, it is particularly important to find a new synthetic method for its development in application. Among them, the Heck reaction is one of the effective methods for the synthesis of compounds such as aromatic substituted alkenes or allenes. However, for the traditional Heck reaction, cinnamate derivatives are generally obtained, which has certain limitations for the synthesis of substituted olefin compounds with other functional groups. [0003] In...

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): C07C43/215C07C43/225C07C41/30C07C25/28C07C17/263C07C15/52C07C1/32C07B37/04
Inventor 毛金成屈孝铭李廷义
Owner SUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com