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Method for synthesizing aryl acetylene

An arylacetylene and aryl technology, applied in the field of synthesizing arylacetylene, can solve the problems of narrow substrate application range, harsh reaction conditions, many by-products, etc., and achieve great use value and social and economic benefits, and the purification method is simple and convenient. The effect of less pollutants

Inactive Publication Date: 2014-04-30
SHANDONG YANHAI CONSTR RESOURCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The above synthetic methods all have the disadvantages of narrow application range of substrates, harsh reaction conditions, many by-products, and large pollution.

Method used

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  • Method for synthesizing aryl acetylene
  • Method for synthesizing aryl acetylene
  • Method for synthesizing aryl acetylene

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Synthesis of 4-methoxyphenylacetylene: Accurately weigh bis(triphenylphosphine)palladium dichloride (8.4g, 12mmol) and cuprous iodide (2.3g, 12mmol) into a 1L three-necked flask, Replaced with nitrogen three times, then added 4-bromoanisole (74.8g, 400mmol) and triethylamine (600mL), stirred at room temperature for 10min, then added trimethylsilylacetylene (68mL, 48mmol), and refluxed at 90°C until complete reaction;

[0030] Cool the above reaction solution to room temperature, filter to remove solid impurities, remove triethylamine (recyclable) by rotary evaporation, and obtain ((4-methoxyphenyl)ethynyl)trimethylamine by recrystallization from petroleum ether-dichloromethane Silica-based, white solid.

[0031] Add the above white solid into a 1L single-necked bottle, add anhydrous potassium carbonate (553mg, 4mmol), ethanol (400mL), stir at room temperature for 1 hour, then remove the solvent by rotary evaporation, and distill under reduced pressure to obtain 4-methox...

Embodiment 2

[0034] Synthesis of 4-fluorophenylacetylene: Accurately weigh tetrakistriphenylphosphine palladium (13.8g, 12mmol) and cuprous oxide (0.72g, 5mmol), add them to a 1L three-necked flask, replace with nitrogen three times, add 4-fluorobromo Benzene (700g, 400mmol), tributylamine (600mL), stir at room temperature for 20min, then add trimethylsilylacetylene (57mL, 40mmol), and react until complete at 50°C;

[0035] Cool the above reaction solution to room temperature, filter to remove solid impurities, remove tributylamine (recyclable) by rotary evaporation, and recrystallize from petroleum ether-dichloromethane to obtain ((4-fluorophenyl)ethynyl)trimethylsilyl , white solid.

[0036] Add the above-mentioned white solid into a 1L single-necked bottle, add anhydrous potassium carbonate (553mg, 4mmol), ethanol (400mL), stir at room temperature for 1 hour, then spin evaporate to remove the solvent, and distill under reduced pressure to obtain 4-fluorophenylacetylene. The yield 91%, ...

Embodiment 3

[0039] 3,4-Difluorophenylacetylene: Accurately weigh bis(triphenylphosphine)palladium dichloride (8.4g, 12mmol) and cuprous oxide (0.86g, 6mmol), add them to a 1L three-necked flask, and replace with nitrogen three times , add 3,4-difluorobromobenzene (772g, 400mmol), diisopropylethylamine (600mL), stir at room temperature for 20min, then add trimethylsilylacetylene (57mL, 40mmol), and react until complete at 50°C;

[0040] Cool the above reaction solution to room temperature, filter to remove solid impurities, remove diisopropylethylamine (recyclable) by rotary evaporation, and obtain ((3,4-difluorophenyl)acetylene by recrystallization from petroleum ether-dichloromethane Base) trimethylsilyl, white solid.

[0041] Add the above white solid into a 1L single-necked bottle, add anhydrous potassium carbonate (553mg, 4mmol), ethanol (400mL), stir at room temperature for 1 hour, then remove the solvent by rotary evaporation, and distill under reduced pressure to obtain 3,4-fluorop...

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Abstract

The invention relates to a method for synthesizing aryl acetylene. The method comprises the following synthesis steps that: (1) coupling reaction is performed, namely, a catalyst, a solvent and bromo-aromatic hydrocarbon are sequentially added in a reactor, and are put in an oil bath for reacting for 5-20 min; then, a trimethylsilylacetylene solution is added, and the mixture is continuously put in the oil bath for reacting completely, wherein the reaction temperature is 80-120 DEG C; (2) the obtained reaction liquid is recrystallized to obtain an intermediate product; (3) the alkaline hydrolysis is performed on the intermediate product; finally, the aryl acetylene is obtained through recrystallization or distillation. The method has the benefits of short synthesis route, mild condition, no by-product, few pollutants, simple purification method and easiness in realization of industrialization; the organic solvent is a single solvent capable of being recycled; as terminal alkyne is an important chemical raw material, and is widely applied in the pharmaceutical field, the method has greater application value and social and economic benefits.

Description

technical field [0001] The invention relates to a method for synthesizing aryl acetylene, in particular to a method for synthesizing aryl acetylene based on brominated aromatic hydrocarbons. Background technique [0002] Alkynes play an important role in chemistry, especially modern organic chemistry, and can undergo dozens of types of reactions to transform into various functional groups. Such as Pauson-Khand reaction (Lee, H.W.; Kwang, F.Y. Adecade of advacements in Pauson-Khand-Type Reaction. Eur. J. Org. Chem. 2010, 789-811), Songashira reaction (Chinchilla, R.; Najerac, C .;The Sonogashira reaction:A Booming Methodology in Synthetic Organic Chemmistry.Chem Rev.2007,107,874-922.), Larock Indole Synthesis (Battistuzzi,G.;Cacchi,S.;Fabrizi,G.The Aminopalladation / Reductive Elimination Domino Reaction in The Construction of Fuctinalized Indole Rings. Eur. J. Org. Chem, 2002, 2671-2681.) et al. Alkynes are also present in many drugs, such as the anticancer drug terbinafine,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/18C07C43/215C07C17/35C07C25/24C07C15/58C07C1/32C07C13/28C07C45/65C07C47/548
CPCC07C41/18C07C1/32C07C13/28C07C15/58C07C17/35C07C25/24C07C43/215C07C45/65C07C47/548
Inventor 王良广谭德敏梁烁梁刚
Owner SHANDONG YANHAI CONSTR RESOURCES
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