A kind of method utilizing continuous flow reactor to produce 3-difluoromethoxy-5-fluorophenylboronic acid

A technology of difluoromethoxy and fluorobenzene boronic acid, which is applied in the synthesis field of producing 3-difluoromethoxy-5-fluorobenzene boronic acid, can solve the problem of low purity and yield of the target product, many side reactions, and high energy efficiency. problems such as large consumption, to achieve the effect of short reaction time, increase conversion rate, and reduce side reactions

Active Publication Date: 2018-08-24
DALIAN JOIN KING FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the conditions of the two methods are relatively strict, especially the use of lithiation reagents is generally required to be around -70 ° C, conventional tank reactors will inevitably cause problems such as local overheating due to uneven mixing, and side reactions in the reaction process Many, the purity and yield of the target product are not high, and the energy consumption is relatively large

Method used

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  • A kind of method utilizing continuous flow reactor to produce 3-difluoromethoxy-5-fluorophenylboronic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] After the two microchannel reactors A1 and A2 are connected in parallel, they are connected in series with the two microchannel reactors B and C successively, and the microchannel reactors are replaced with anhydrous tetrahydrofuran;

[0018] Weigh 242 g of 3-difluoromethoxy-5-fluorobromobenzene and 226 g of triisopropyl borate and dissolve in 1500 g of tetrahydrofuran to form a homogeneous solution with a volume of about 1900 mL; weigh 1.6 M / L n-butyl Lithium n-hexane solution 810 mL;

[0019] Control the flow rate of the mixed solution of 3-difluoromethoxy-5-fluorobromobenzene to 80 mL / min; control the flow rate of n-butyllithium solution to 35 mL / min, and the two streams of materials flow through the A1 and A2 microreactions respectively The reactor is pre-cooled (-30°C), and then enters the microreactors B and C at the same time; the reaction residence time is 8.3s, and the reaction temperature is -30°C;

[0020] The outlet reaction solution was added dropwise to 1...

Embodiment 2

[0023] After the two microchannel reactors A1 and A2 are connected in parallel, they are connected in series with the two microchannel reactors B and C successively, and the microchannel reactors are replaced with anhydrous tetrahydrofuran;

[0024] Weigh 242 g of 3-difluoromethoxy-5-fluorobromobenzene and 125 g of trimethyl borate and dissolve in 1500 g of tetrahydrofuran to form a homogeneous solution with a volume of about 1900 mL; weigh 2.5 M / L n-butyllithium 600 mL of n-hexane solution;

[0025] Control the flow rate of the mixed solution of 3-difluoromethoxy-5-fluorobromobenzene to 80 mL / min; control the flow rate of n-butyllithium solution to 25 mL / min, and the two materials flow through the A1 and A2 microreactions respectively The reactor is pre-cooled (-30°C), and then enters the microreactors B and C at the same time; the reaction residence time is 9.1s, and the reaction temperature is -30°C;

[0026] The outlet reaction solution was added dropwise to 10% dilute hy...

Embodiment 3

[0028] After the two microchannel reactors A1 and A2 are connected in parallel, they are connected in series with the two microchannel reactors B and C successively, and the microchannel reactors are replaced with anhydrous tetrahydrofuran;

[0029] Weigh 242 g of 3-difluoromethoxy-5-fluorobromobenzene and 226 g of triisopropyl borate and dissolve in 1500 g of tetrahydrofuran to form a homogeneous solution with a volume of about 1900 mL; measure 2.5 M / L n-butyl Lithium n-hexane solution 600 mL;

[0030] Control the flow rate of the mixed solution of 3-difluoromethoxy-5-fluorobromobenzene to 80 mL / min; control the flow rate of n-butyllithium solution to 25 mL / min, and the two materials flow through the A1 and A2 microreactions respectively The reactor is pre-cooled (-10°C), and then enters the microreactors B and C at the same time; the reaction residence time is 9.1s, and the reaction temperature is -10°C;

[0031] The outlet reaction solution was added dropwise to 10% dilute...

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Abstract

The invention discloses a synthesis process for producing 3-difluoromethoxy-5-fluorophenylboronic acid by a micro-passage continuous flow reactor, and belongs to the technical field of fine chemical engineering intermediate synthesis processes. According to the process, 3-difluoromethoxy-5-bromopentafluorobenzene, borate and n-butyllithium are used as raw materials to take a reaction in the micro-passage continuous flow reactor. The process has the advantages that the reaction speed is high; the production period is short; ultra-low-temperature reaction conditions are avoided; side reactions are few; products can be easily purified.

Description

technical field [0001] The invention relates to a synthesis method for producing 3-difluoromethoxy-5-fluorophenylboronic acid by using a microchannel continuous flow reactor, and belongs to the field of fine chemical synthesis technology. Background technique [0002] 3-Difluoromethoxy-5-fluorophenylboronic acid or borate is an important fine chemical intermediate, mainly used to prepare high-performance liquid crystal materials and pharmaceutical intermediates, and its market demand is increasing, and Quality requirements are getting higher and higher. Therefore, the research on the synthetic method of 3-difluoromethoxy-5-fluorophenylboronic acid or borate has practical significance. [0003] At present, the synthesis of 3-difluoromethoxy-5-fluorophenylboronic acid has not been reported in public information, and only one patent US2014371201 reported the synthesis of 3-difluoromethoxy-5-fluorophenylboronic acid ester. Homogeneous palladium catalyzes the reaction of 3-difl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02B01J19/00
CPCB01J19/0093C07F5/025
Inventor 李雨王海英吕超王俊春李殿虎王荣良
Owner DALIAN JOIN KING FINE CHEM CO LTD
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