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

Method for synthesizing 1-iodo-alkyne in high-selectivity manner

A highly selective, iodo-based technology, applied in organic chemistry methods, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of using metal catalysts, harsh reaction conditions, uncontrollable reactions, etc. The effect of mild conditions and easy separation and purification

Active Publication Date: 2017-06-13
GUANGDONG UNIV OF TECH
View PDF0 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional methods for synthesizing iodoalkyne compounds are mainly metal catalysis, base catalysis and phase transfer catalysis, which often require the use of ultrasonic waves, Grignard reagents and lithium reagents for the synthesis reaction. The reaction conditions are harsh, the selectivity is low, and the reaction is uncontrollable. , need to use metal catalysts, pollute the environment and other problems

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 synthesizing 1-iodo-alkyne in high-selectivity manner
  • Method for synthesizing 1-iodo-alkyne in high-selectivity manner
  • Method for synthesizing 1-iodo-alkyne in high-selectivity manner

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Dissolve 38 μL (0.3 mmol) of p-methylphenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide (TBAI) in 3 mL of acetonitrile, then add 96.6 mg (0.3 mmol) of iodobenzenediacetic acid in portions within 30 min into the reaction system, react at room temperature for 24 h, and then extract three times with ethyl acetate, combine the organic phases and concentrate under reduced pressure to obtain the crude product 1. The crude product 1 was separated and purified by silica gel column chromatography (n-hexane 100%) to obtain 71.9 mg of yellow liquid product 1 with a yield of 99%. The NMR data are as follows:

[0034] ( 1 H NMR, 400MHz, CDCl 3 , ppm): δ=7.32(d, J=8.0Hz, 2H), 7.10(d, J=8.0Hz, 2H), 2.34(s, 3H);

[0035] ( 13 C NMR, 100MHz, CDCl 3 , ppm): δ=139.1, 132.3, 129.0, 120.4, 94.3, 21.6.

Embodiment 2

[0037]

[0038] 33 μL (0.3 mmol) of phenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide were dissolved in 3 mL of acetonitrile, and then 96.6 mg (0.3 mmol) of iodobenzenediacetic acid was added to the reaction system in batches within 30 min. After reacting at room temperature for 24 h, and then extracting three times with ethyl acetate, the organic phases were combined and concentrated under reduced pressure to obtain the crude product 2. The crude product 2 was separated and purified by silica gel column chromatography (n-hexane 100%) to obtain 62.6 mg of yellow liquid product 2 with a yield of 92%. The NMR data are as follows:

[0039] 1 H NMR (400MHz, CDCl 3 ,ppm): δ=7.41-7.43(m,2H),7.29-7.31(m,3H);

[0040] 13 C NMR (100 MHz, CDCl3, ppm): δ = 132.4, 128.8, 128.3, 123.4, 94.2, 6.2.

Embodiment 3

[0042]

[0043] Dissolve 34.4 μL (0.3 mmol) of 4-fluorophenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide in 3 mL of acetonitrile, then add 193.3 mg (0.6 mmol) of iodobenzenediacetic acid to the reaction in batches within 30 min In the system, react at room temperature for 2 h, and then extract three times with ethyl acetate, combine the organic phases and concentrate under reduced pressure to obtain the crude product 3. The crude product 3 was separated and purified by silica gel column chromatography (n-hexane 100%) to obtain 67.8 mg of yellow liquid product 3 with a yield of 92%. The NMR data are as follows:

[0044] 1 H NMR (400MHz, CDCl 3 , ppm): δ=7.42-7.40(m, 2H), 7.01(t, J=8.8Hz, 2H);

[0045] 13 C NMR (100MHz, CDCl 3 , ppm): δ=162.7 (d, J=249Hz), 134.3 (d, J=8.4Hz), 119.5 (d, J=3.5Hz), 115.7 (d, J=22.1Hz), 93.0, 5.9.

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 belongs to the technical field of synthetic chemistry and particularly relates to a method for synthesizing 1-iodo-alkyne in a high-selectivity manner. The method is mild in reaction condition, controllable in reaction product, single in product, easy in product purification, high in chemical selectivity, simple in synthesizing step, safe, reliable, green, environmentally friendly, applicable to various terminal alkyne reaction substrates and suitable for industrial production, and the synthesizing yield of the method reaches up to 99%.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, and in particular relates to a method for synthesizing 1-iodoalkyne with high selectivity. Background technique [0002] Iodoalkyne compounds are an important class of organic synthesis intermediates, which can be used to construct important molecular skeletons of fine chemicals, drug molecules and functional materials or as reaction precursors. It has important biological activity and has a wide range of applications in the fields of medicinal chemistry, applied chemistry and synthetic chemistry, and its synthesis and application are of great research value. Among them, the oxidative iodination reaction of alkynes is an important method for the synthesis of iodoalkyne compounds. [0003] The traditional methods for synthesizing iodoalkyne compounds are mainly metal catalysis, base catalysis and phase transfer catalysis, which often require the use of ultrasonic waves, Grignard reage...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07B39/00C07C22/04C07C17/14C07C22/08C07C21/22C07C33/42C07C29/62C07C69/76C07C67/307C07C67/287C07C69/145C07C233/07C07C231/12C07D333/12C07F7/08
CPCC07B39/00C07C17/14C07C29/62C07C67/287C07C67/307C07C231/12C07D333/12C07F7/081C07F7/083C07C22/04C07C22/08C07C21/22C07C33/426C07C69/76C07C69/145C07C233/07
Inventor 刘艳黄达涯王德安黄菊赖炳森丸岡啓二
Owner GUANGDONG UNIV OF TECH
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