Synthesis method of 4-cyclopentyl biphenyl fluorinated compound

A technology of cyclopentyl biphenyl and cyclopentenyl biphenyl is applied in the field of synthesizing fluorine-containing compounds of 4-cyclopentyl biphenyl, and can solve the problem of low yield of fluorine-containing compound IX, high environmental protection pressure and shortened service life of facilities and other problems, to achieve the effect of convenient post-processing, high safety performance, and low environmental pollution.

Active Publication Date: 2018-06-22
山东盛华新材料科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology offers several benefits compared to current methods such as synthesis or expensive starting materials like p-bimonylbenzene (pMB). These technical improvements include improved efficiency, reduction on costs, higher yields, safer handling during manufacturing processes, enhanced safety fidelity, ease of use after treatment, and minimal waste generated from these new techniques.

Problems solved by technology

This patented technical problem addressed by this patents relates to improving the efficiency or safety of making certain types of chemical substances that contain boron atoms (B) with specific functions such as pharmaceutical agents like clobazam).

Method used

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  • Synthesis method of 4-cyclopentyl biphenyl fluorinated compound
  • Synthesis method of 4-cyclopentyl biphenyl fluorinated compound
  • Synthesis method of 4-cyclopentyl biphenyl fluorinated compound

Examples

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Embodiment 1

[0018] Example 1, a synthesis method of 4-cyclopentylbiphenyl fluorine-containing compound IX, this embodiment is a synthesis method of 4'-cyclopentyl-3,5-difluorobiphenyl, the synthesis route is as follows:

[0019]

[0020]

[0021] Wherein the preparation of 4-cyclopentenyl chlorobenzene V is: under the protection of inert gas, in the 500ml reaction bottle that mechanical stirring, reflux condensation drying tube, feeding funnel are housed, add magnesium sheet 13g, THF35ml successively, stir; To 50°C, add dropwise 20ml of the prepared p-chlorobromobenzene 100g / THF100ml mixed solution into the system, the reaction is initiated, and the temperature is controlled at 50°C to 70°C to add dropwise. A good cyclopentanone 50g / toluene 200ml mixed solution, stop the reaction 90min after the dropwise addition, pour the reaction solution into a 500ml reaction bottle with 100ml of concentrated hydrochloric acid, stir for 2h, then add 100ml of toluene, stir for 1h and let it stand ...

Embodiment 2

[0025] Example 2, a synthesis method of 4-cyclopentylbiphenyl fluorine-containing compound IX, this embodiment is a synthesis method of 4'-cyclopentyl-3,4,5-trifluorobiphenyl, the synthesis route is as follows:

[0026]

[0027] Wherein the preparation of 4-cyclopentenyl chlorobenzene V is: under the protection of inert gas, in the 500ml reaction bottle that mechanical stirring, reflux condensation drying tube, feeding funnel are housed, add magnesium sheet 13g, THF35ml successively, stir; To 70°C, add dropwise 20ml of the prepared p-dichlorobenzene 77g / THF100ml mixed solution into the system, the reaction is initiated, and the temperature is controlled at 70°C to 80°C to add dropwise. A good cyclopentanone 50g / toluene 200ml mixed solution, 120min after the dropwise addition, stop the reaction, pour the reaction solution into a 500ml reaction bottle with 100ml of concentrated hydrochloric acid, stir for 2h, then add 100ml of toluene, stir for 1h and let it stand Separate th...

Embodiment 3

[0031] Embodiment 3, a synthetic method of 4-cyclopentylbiphenyl fluorine-containing compound IX, this embodiment is a synthetic method of 4'-cyclopentyl-3-fluorobiphenyl, the synthetic route is as follows:

[0032]

[0033] Wherein the preparation of 4-cyclopentenyl chlorobenzene V is: under the protection of inert gas, in the 500ml reaction bottle that mechanical stirring, reflux condensation drying tube, feeding funnel are housed, add magnesium sheet 13g, THF35ml successively, stir; To 70°C, add dropwise 20ml of the prepared p-chloroiodobenzene 125g / THF100ml mixed solution into the system, the reaction is initiated, and the temperature is controlled at 40°C to 50°C to add dropwise. A good cyclopentanone 50g / toluene 200ml mixed solution, 120min after the dropwise addition, stop the reaction, pour the reaction solution into a 500ml reaction bottle with 100ml of concentrated hydrochloric acid, stir for 2h, then add 100ml of toluene, stir for 1h and let it stand Separate the...

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Abstract

The invention provides a synthesis method of a 4-cyclopentyl biphenyl fluorinated compound. The method comprises the steps of taking p-chloro-halobenzene as a starting material and carrying out Grignard reaction to generate a Grignard reagent II of the p-chloro-halogenated benzene; enabling the generated Grignard reagent II of the p-chloro-halogenated benzene and cyclopentanone to be subjected toa coupling reaction to generate cyclopentanol chlorobenzene; carrying out a dehydration reaction to generate cyclopentene chlorobenzene; carrying out a one-pot reaction to generate 4-cyclopentenyl phenylboronic acid; enabling the generated 4-cyclopentenyl phenylboronic acid and fluorinated halogenated benzene to be subjected to a coupling reaction to generate a 4-cyclopentenyl biphenyl fluorinatedcompound; carrying out a hydrogenation reaction to obtain the 4-cyclopentyl biphenyl fluorinated compound. The synthesis method provided by the invention has the characteristics of being high in conversion rate, low in cost, safe and stable in process, short in reaction steps, environmentally friendly in process route, and less in pollutant emission.

Description

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Claims

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Application Information

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Owner 山东盛华新材料科技股份有限公司
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