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Process for the preparation of fluorophenylalkylene acid derivatives

A technology for fluorophenyl alkylene carboxylic acid and derivatives, which is applied in the field of preparing fluorophenyl alkylene acid derivatives and can solve problems such as low yields

Inactive Publication Date: 2008-04-02
DIC CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively low yields and problems with by-products such as bisaryl

Method used

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  • Process for the preparation of fluorophenylalkylene acid derivatives
  • Process for the preparation of fluorophenylalkylene acid derivatives
  • Process for the preparation of fluorophenylalkylene acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] To a suspension of magnesium (0.132 moles, 3.2 g) in THF was added dropwise a solution of 1-bromo-3,4,5-trifluorobenzene (0.132 moles, 27.8 g) in THF. After the exothermic reaction had died down, the reaction mixture was refluxed for 30 minutes. To a stirred solution of anhydrous zinc chloride (0.132 mol, 18 g) in THF cooled to 0°C was added dropwise the Grignard solution. When the dropwise addition was complete, the solution was stirred at room temperature for an additional 30 minutes. The reaction mixture was cooled to 0°C, ethyl bromoacetate (0.11 mol, 18.4 g) and catalyst bis(acetylacetonate)-2,2'-bipyridine nickel(II) (0.4 mmol, 219 mg, 0.5 mol%) were added ). The reaction was kept at 5°C overnight. The solution was quenched with ice / water and extracted with ether. The organic layer was washed with saturated sodium chloride solution. After drying over sodium sulfate, the solvent was evaporated. The crude product was purified by distillation, isolated yield: 1...

Embodiment 2

[0104] To a stirred solution of 1,2-difluorobenzene in THF cooled to -78°C was added dropwise a solution of n-butyllithium (1.3 mmol) in hexane. After stirring at -78°C for 1 h, a solution of anhydrous zinc chloride (1.3 mmol) in THF was added dropwise, and the mixture was allowed to warm to room temperature. The solution was stirred at room temperature for 1 hour and cooled to 0 °C. Ethyl bromoacetate (1.3 mmol) and the catalyst bis(acetylacetonate)-2,2'-bipyridine nickel(II) (0.4 mmol / 0.5 mol%) were added, then the reaction was kept at room temperature overnight. The solution was quenched with ice / water and extracted with ether. The organic layer was washed with saturated sodium chloride solution. After drying over sodium sulfate, the solvent was evaporated. The crude product was purified by distillation. The yield was 77%.

Embodiment 3

[0106] According to the method of Example 2, ethyl 2-(2,3-difluorophenyl)acetate was produced from 1,2-difluorobenzene and ethyl bromoacetate. Different from Example 2, the molar ratio of aryl compound and ester was 1.5:1, and the reaction time was 1 hour. The yield was 74%.

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Abstract

The present invention provides a new method for producing phenylalkylenecarboxylic acid derivatives.

Description

Background technique [0001] Phenylacetic acid and its esters and their derivatives, especially those containing one or more than one substituent on the benzene ring, are interesting starting compounds for active ingredients in pharmaceuticals and pesticides. Documented is the use of phenylacetic acid, for example for the preparation of medicaments of the dibenzocycloheptatriene type as described in DE 1593314, and for the types "Varzac" and "fenbufen". " type analgesics. [0002] Various methods are known for the preparation of unsubstituted and aryl-substituted phenylacetic acids and their derivatives. A. Burger and S. Avakian describe the preparation of (4-methoxyphenyl)acetic acid from 4-methoxybenzoic acid via the corresponding α-diazomethanone and its rearrangement to phenylacetic acid. A.McKillop etc. described in J.Am.Chem.Soc 95,3340 (1973) by T l(NO on Montmorillonit-K10 3 ) 3 mediated, oxidative rearrangement of many aryl-substituted acetophenones to the correspo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/65C07C67/30C07C67/307C07B61/00C07C67/343
CPCC07C67/343C07C69/65
Inventor 托马斯·德勒赖纳·B·弗林斯科妮莉亚·皮特哈特格瓦尔德·格拉厄
Owner DIC CORPORATION
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