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Synthetic method of diarylethene

A technology of diarylethene and synthesis method, which is applied in chemical instruments and methods, preparation of hydroxy compounds, separation/purification of hydroxy compounds, etc., can solve the problems of complex methods and low efficiency of diarylene, and achieve simple operation, The effect of economical ratio of reaction feed and high-efficiency catalytic cycle

Active Publication Date: 2018-05-29
LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the efficiency of Heck reaction synthesis method to obtain diarylethene is low and the method is complicated, so it is necessary to develop a simple and efficient synthetic method

Method used

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  • Synthetic method of diarylethene
  • Synthetic method of diarylethene
  • Synthetic method of diarylethene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] This example prepares 1,2-dibenzocyclobutenylethylene, the specific steps and conditions are:

[0027] In a clean and dry anaerobic bottle, add 5.9g of potassium acetate and 5mL of ultrapure water, stir to dissolve. After dissolving, add 10mL of re-distilled N,N-dimethylformamide to perform a deoxygenation treatment. After the treatment was completed, 7.48g of 4-bromobenzocyclobutene, 1.86g of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 23mg of palladium acetate, and 60mg of tri-o-toluene were sequentially added Phosphine, 6.5g tetrabutylammonium bromide. After the drug was added, another deoxygenation treatment was carried out, nitrogen gas was introduced, the reaction bottle was placed in an oil bath, the temperature was raised to 100°C, and the reaction was stirred for 48 hours. After the reaction, cool to room temperature. Use 200 mL of ethyl acetate for extraction, wash with water three times, add 30 mL of water each time, and wash once with saturated brine, sepa...

Embodiment 2

[0032] In this example, 1,2-bis(1-hydroxymethylbenzocyclobutene) ethylene was prepared. The specific steps and conditions are as follows:

[0033] In a clean and dry anaerobic bottle, add 5.9g of potassium acetate and 5mL of ultrapure water, stir to dissolve. After dissolving, add 10mL of re-distilled N,N-dimethylformamide to perform a deoxygenation treatment. After the treatment is completed, add 8.68g 4-bromo-1-hydroxymethylbenzocyclobutene, 1.86g 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 23mg acetic acid Palladium, 60 mg tri-o-tolylphosphine, 6.5 g tetrabutylammonium bromide. After the drug was added, another deoxygenation treatment was carried out, nitrogen gas was introduced, the reaction bottle was placed in an oil bath, the temperature was raised to 100°C, and the reaction was stirred for 48 hours. After the reaction, cool to room temperature. Use 200 mL of ethyl acetate for extraction, wash with water three times, add 30 mL of water each time, and wash once with sa...

Embodiment 3

[0035] In this example, 1,2-bis(1-carboxybenzocyclobutene) ethylene was prepared. The specific steps and conditions are as follows:

[0036] In a clean and dry anaerobic bottle, add 5.9g of potassium acetate and 5mL of ultrapure water, stir to dissolve. After dissolving, add 10mL of re-distilled N,N-dimethylformamide to perform a deoxygenation treatment. After the treatment was completed, 9.24g of 4-bromo-1-carboxybenzocyclobutene, 1.86g of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 23mg of palladium acetate, 60mg tri-o-tolylphosphine, 6.5g tetrabutylammonium bromide. After the drug was added, another deoxygenation treatment was carried out, nitrogen gas was introduced, the reaction bottle was placed in an oil bath, the temperature was raised to 100°C, and the reaction was stirred for 48 hours. After the reaction, cool to room temperature. Use 200 mL of ethyl acetate for extraction, wash with water three times, add 30 mL of water each time, and wash once with saturated brin...

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Abstract

The invention discloses a synthetic method of diarylethene. The method comprise the following steps: potassium acetate and ultrapure water are added to a dry anaerobic tube, and stirred to be dissolved; then re-steamed N,N-dimethylformamide is added, and nitrogen is introduced for deoxygenation; reactants aryl bromide and 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, catalyst palladium acetate, ligand tri-o-tolylphosphine and additive tetrabutylammonium bromide are added sequentially, nitrogen is introduced for deoxygenation, temperature is increased to 100 DEG C, and stirring is performed untila reaction is finished; diarylethene with yield as high as 90% or higher is obtained finally through a post-processing procedure. With adoption of the synthetic method of diarylethene, yield is high,ethylene gas and a pressure container not easy to operate are not needed, and the synthetic method can be widely applied to industrial production and has better market application prospect.

Description

technical field [0001] The invention belongs to the technical field of small organic molecule synthesis methods, and in particular relates to a synthesis method of diarylethene. Background technique [0002] The materials prepared by benzocyclobutene (Benzocyclobutene, BCB) and its derivatives have good thermal stability, machinability, moisture resistance, especially excellent low dielectric properties, film-forming properties, etc. It has been widely used in military and civilian fields such as microelectronics and aerospace. 1,2-Dibenzocyclobutenylethylene, as a special diarylethene compound, has a four-membered ring structure that can be ring-opened and cross-linked due to its special chemical structure, as shown in formula (I), and can The double bond structure with Diels-Alder reaction has high heat resistance and excellent low dielectric properties, making it especially suitable for high-performance casting resin matrix or high-performance composite material resin ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/32C07C7/00C07C7/10C07C7/14C07C15/52C07C13/44C07D333/08C07C253/30C07C253/34C07C255/47C07C51/353C07C51/48C07C51/43C07C61/39C07C29/32C07C29/86C07C29/78C07C35/31
CPCC07C1/321C07C7/005C07C7/10C07C7/14C07C29/32C07C29/78C07C29/86C07C51/353C07C51/43C07C51/48C07C253/30C07C253/34C07C2531/22C07D333/08C07C15/52C07C13/44C07C255/47C07C61/39C07C35/31
Inventor 尹强张帅卢春林李娃朱方华王宇光徐嘉靖
Owner LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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