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Preparation method of functionalized aryl acetate compound

A technology of aryl acetate and functional grouping, which is applied in the field of preparation of aryl acetate compounds, can solve problems such as narrow scope of application, and achieve the effects of good compatibility and high yield

Inactive Publication Date: 2012-07-25
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above two methods must be reacted under alkaline conditions, so the above method has a high selectivity to reactants, and is not suitable for compounds containing unstable groups to alkalis as reactants, and the scope of application is narrow

Method used

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  • Preparation method of functionalized aryl acetate compound
  • Preparation method of functionalized aryl acetate compound
  • Preparation method of functionalized aryl acetate compound

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preparation example Construction

[0057] In the preparation method provided by the present invention, the above-mentioned reactant is preferably placed in the following organic solvent for reaction: benzene, toluene, xylene, 1,3,5-trimethylbenzene, dimethyl sulfoxide, N,N-dimethyl Formamide, N,N-dimethylacetamide, N-methylpyrrolidone, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, or dipropylene glycol diethyl ether. The inert gas can be a gas well known to those skilled in the art, such as argon or nitrogen atmosphere. The reaction temperature is preferably 120°C to 140°C, and the reaction is completed after 10 to 30 hours of reaction time, and then the product is purified as follows:

[0058] After the reaction system mixture that has been reacted is filtered, the filtrate is chromatographed using fast silica gel column chromatography, and the reaction solvent is first eluted with petroleum ether, and then the mixed solvent eluent of petroleum ether and ...

Embodiment 1

[0061] Embodiment 1 prepares ethyl phenylacetate

[0062] 1. Add 0.75 mmol of monoethyl malonate potassium salt, 0.01 mmol of allyl palladium chloride and 0.03 mmol of 2-bicyclohexylphosphine-2', 6'-diisopropoxy in a vacuum reactor Base biphenyl, vacuumize, connect high-purity argon, replace three times, add 0.5mmol of chlorobenzene and organic solvent trimethylbenzene under the protection of argon flow, the addition of organic solvent adds 2 In milliliters of solvent, the mixture in the reactor was heated to 120° C., and the reaction was terminated after heating and stirring for 10 hours. The reaction of this step is as follows:

[0063]

[0064] 2. Purify the reaction system mixture after the reaction with fast silica gel column chromatography, first use 50mL of petroleum ether to elute the solvent trimethylbenzene, and then use petroleum ether and ethyl acetate as an eluent with a volume ratio of 50:1. The product ethyl phenylacetate was obtained in 83% yield.

[0065...

Embodiment 2

[0066] Embodiment 2 prepares 2-(2-thienyl) ethyl acetate

[0067] 1. Add 0.75mmol of monoethyl malonate potassium salt, 0.01mmol of allyl palladium chloride (Pd2(p-allyl)2Cl2) and 0.03mmol of 2-bicyclohexylphosphine-2 in the vacuum reactor ', 6'-diisopropoxybiphenyl, vacuumize, pass through high-purity argon, replace three times, add 0.5mmol of pro-2-chlorothiophene and organic solvent trimethylbenzene under the protection of argon flow, and organic solvent The addition amount is based on the addition of 2 milliliters of solvent per millimole of the electrophilic substrate, and the mixture in the reactor is heated to 140° C., and the reaction is terminated after heating and stirring for 20 hours. The reaction of this step is as follows:

[0068]

[0069] 2. Purify the reaction system mixture after the reaction with fast silica gel column chromatography, first use 50mL of petroleum ether to elute the solvent trimethylbenzene, and then use petroleum ether and ethyl acetate a...

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Abstract

The invention provides a preparation method of a functionalized aryl acetate compound. The preparation method comprises the following step of carrying out decarboxylation coupling reaction on a decarboxylation coupling reagent and an electrophilic substrate in an organic solvent in the presence of a palladium catalyst and a phosphine ligand under the protection of inert gas to obtain the functionalized aryl acetate compound. According to the preparation method, the conjugation use of the palladium catalyst and the phosphine ligand can well catalyze the decarboxylation coupling reagent and the electrophilic substrate, and alkali does not need to be added in the reaction process, thus the method provided by the invention has good compatibility with a reactant sensitive to alkali. In addition, the yield of the functionalized aryl acetate compound prepared by using the preparation method provided by the invention is high; and an experiment proves that the yield of a target product reaches more than 78%.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of functionalized aryl acetate compounds. Background technique [0002] Aryl acetate is a compound with (I) structure, R is an alkyl group in formula (I), and a functional group is inserted on the aryl acetate benzene ring to obtain functionalized aryl acetate compounds . Functionalized aryl acetate compounds are important intermediates of anti-inflammatory analgesics such as ibuprofen, such as ethyl 2-(4'-isobutylphenyl) propionate is ibuprofen 2-(4'- An important intermediate of isobutylphenyl)propionic acid, ethyl 2-(3'-fluoro-4'-phenylphenyl)propionate is flurbiprofen 2-(3'-fluoro-4'-benzene An important intermediate of phenyl)propionic acid. [0003] [0004] At present, the preparation method of the reported functionalized aryl acetate compound mainly contains following two kinds: [0005] The first method is that phenylboronic acid and ethyl bro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/614C07C69/616C07C67/30C07D333/24C07D213/55C07D215/10
Inventor 尚睿计东生傅尧郭庆祥刘磊
Owner UNIV OF SCI & TECH OF CHINA
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