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Method for synthesizing ibuprofen and analogues thereof

A technology of compounds and substances, applied in the field of compound synthesis, can solve problems such as insufficient safety

Inactive Publication Date: 2011-04-13
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among these methods, the traditional synthetic method has too many steps. Although the recent synthetic method has simplified steps, it needs to use highly toxic carbon monoxide gas, which is not safe enough.

Method used

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  • Method for synthesizing ibuprofen and analogues thereof
  • Method for synthesizing ibuprofen and analogues thereof
  • Method for synthesizing ibuprofen and analogues thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0160](1) Preparation of 2-(4-isobutylphenyl) propionitrile

[0161] In an oven-dried 100 mL Schlenk flask equipped with a magnet, add dipolyallylpalladium chloride (0.0146 g, 0.040 mmol), 9,9-dimethyl-4,5-bis(di tert-butylphosphino)xanthene (0.0693 g, 0.120 mmol), 1-bromo-4-isobutylbenzene (8.52 g, 40 mmol) and potassium 2-cyanopropionate (6.58 g, 48 mmol). The lid is coated with a vacuum grease grinding plug, connected to the Schrank vacuum line, the air in the container is drained and filled with nitrogen, repeat 3 times, and 40mL of mesitylene is added under the reverse flow of nitrogen. After the addition, cover with a stopper, put it into a 140°C oil pan after clamping, and stir for 20 hours. After the reaction was completed, it was directly separated by chromatographic column to obtain a light yellow liquid with a yield of 96%.

[0162] (2) Preparation of 2-(4-isobutylphenyl) propionic acid

[0163] Add 2-(4-isobutylphenyl)propionitrile (5.62g, 30mmol) and sodium hyd...

Embodiment 2

[0165] (1) Preparation of 2-(4-isobutylphenyl) acetonitrile

[0166] In an oven-dried 100 mL Schlenk bottle equipped with a magnet, add dipolyallylpalladium chloride (0.0146 g, 0.040 mmol), 2-bicyclohexylphosphine-2′,6′-dimethoxy phenylbiphenyl (0.0493g, 0.120mmol), 1-chloro-4-isobutylbenzene (6.75g, 40mmol) and sodium cyanoacetate (5.14g, 48mmol). The lid is coated with a vacuum grease grinding plug, connected to the Schrank vacuum line, the air in the container is drained and filled with nitrogen, repeat 3 times, and 40mL of mesitylene is added under the reverse flow of nitrogen. After the addition, cover with a stopper, put it into a 140°C oil pan after clamping, and stir for 20 hours. After the reaction was completed, it was directly separated by chromatographic column to obtain a light yellow liquid with a yield of 97%.

[0167] (2) Preparation of 2-(4-isobutylphenyl) propionitrile

[0168] In a 150ml round bottom flask equipped with a magnet was charged 2-(4-isobutylp...

Embodiment 3

[0173] (1) Preparation of 2-(3-benzoylphenyl) propionitrile

[0174] In an oven-dried 100 mL Schlenk flask equipped with a magnet, add dipolyallylpalladium chloride (0.0146 g, 0.040 mmol), 9,9-dimethyl-4,5-bis(di tert-butylphosphino)xanthene (0.0693 g, 0.120 mmol), 3-bromophenylbenzophenone (10.44 g, 40 mmol) and potassium 2-cyanopropionate (6.58 g, 48 mmol). The lid is coated with a vacuum grease grinding plug, connected to the Schrank vacuum line, the air in the container is drained and filled with nitrogen, repeat 3 times, and 40mL of mesitylene is added under the reverse flow of nitrogen. After the addition, cover with a stopper, put it into a 140°C oil pan after clamping, and stir for 20 hours. After the reaction was completed, it was directly separated by chromatographic column to obtain a light yellow liquid with a yield of 91%.

[0175] (2) Preparation of 2-(3-benzoylphenyl) propionic acid

[0176] Add 2-(3-benzoylphenyl)propionitrile (7.06g, 30mmol) and sodium hydr...

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Abstract

The invention provides a method for synthesizing ibuprofen and analogues thereof. In the method, 1-halogenated-4-isobutylbenzene and cyanogen acetate derivatives are taken as raw materials for synthesizing the ibuprofen; halogenated benzene derivatives and the cyanogen acetate derivatives are taken as raw materials for synthesizing the analogues of the ibuprofen; and the raw materials for synthesizing the ibuprofen and the raw materials for synthesizing the analogues of the ibuprofen are subjected to a palladium catalyzed decarboxylation coupling reaction, a methylation reaction and a hydrolysis reaction to synthesize the ibuprofen and the analogues thereof respectively. The synthesizing method is simple, and easy to operate and has wide raw material sources and low cost, and only inorganic salt and carbon dioxide are produced in the synthesizing process, so that the method is safe and environmentally-friendly, meets the requirement of green chemistry, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for ibuprofen and its analogs. Background technique [0002] The chemical name of ibuprofen is: 2-(4-isobutylphenyl)propionic acid. Its chemical formula is: [0003] [0004] Similar compounds are: [0005] [0006] Ketoprofen Suprofen Phenoxyibuprofen [0007] Ibuprofen (Ibuprofen) was first listed in the UK in 1968, and has been included in the pharmacopoeias of the UK, the US and other countries. Symptoms such as high fever and fever. Ketoprofen, suprofen, and phenoxyibuprofen, which are structurally similar to ibuprofen, are also NSAIDs. [0008] At present, there are many synthetic methods for ibuprofen, mainly Chinese patent CN88102150, Chinese patent CN92106667.8, and Chinese patent CN200910042425.8. In these methods, the traditional synthetic method has too many steps. Although the recent synthetic method has simplified steps, it needs to use highly ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/30C07C51/08C07C59/84C07C59/68C07D333/24
Inventor 尚睿傅尧刘磊
Owner UNIV OF SCI & TECH OF CHINA
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