A kind of preparation method of heterocyclic boronic acid compound

A technology for boronic acid compounds and heterocyclic compounds, which is applied in the field of preparation of heterocyclic boronic acid compounds, can solve problems such as time-consuming, difficult preparation of dibenzofuran-2-boronic acid, and danger of organolithium reagents, so as to increase the reaction temperature and avoid The use of explosive raw materials, the effect of reducing energy consumption and danger

Active Publication Date: 2020-05-15
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Carbazole-2-boronic acid and dibenzofuran-2-boronic acid are intermediate reagents commonly used in organic chemical synthesis, and can be used to prepare a variety of chemical products with special functions. For example, carbazole-2-boronic acid can be used for The preparation of organic light-emitting diode (OLED) thin film displays has many advantages such as thinness, wide viewing angle, low power consumption, and fast response. Dibenzofuran-2-boronic acid can be used to prepare liquid crystal compounds, which are widely used in large display screens, portable In equipment such as computers and navigation systems, however, the preparation of carbazole-2-boronic acid and dibenzofuran-2-boronic acid is relatively difficult, and the common preparation method is by combining halogenated carbazole or halogenated dibenzofuran with organic Lithium reagents are mixed and reacted at -80~-100°C for more than 20 minutes, then boric acid ester is added to react for 30~60 minutes, and hydrolyzed to obtain carbazole-2-boronic acid and dibenzofuran-2-boronic acid products. This process is time-consuming Long, the organolithium reagent used is very dangerous, not suitable for industrialized and continuous production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Prepare dibenzofuran-2-boronic acid by the following method, the preparation method comprising the following steps:

[0034] In step (1), dibenzofuran-2-bromo and triisobutylaluminum are dissolved in tetrahydrofuran at a molar ratio of 1:3 to prepare a solution 1 with a total concentration of 5 mg / mL. Solution 1 is heated at -35°C temperature storage for later use;

[0035] In step (2), tributyl borate is dissolved in ethyl acetate to prepare a solution 2 with a concentration of 10 mg / mL;

[0036] In step (3), both solution 1 and solution 2 are continuously injected into the inflow end of a flow chemical reaction tube with a diameter of 1 mm at a flow rate of 10 mL / min for reaction. The reaction time in the reaction tube is 3 min, and the reaction temperature is 24 ° C. ;

[0037] Step (4), in the outflow end of the flow chemical reaction tube, the reaction solution flowing out is mixed with the sulfuric acid solution with a pH of 1 at a flow ratio of 1:2, and the mix...

Embodiment 2

[0039] Prepare N-methylcarbazole-2-boronic acid by following method, described preparation method comprises the steps:

[0040] In step (1), N-methylcarbazole-2-bromo and triisobutylaluminum are dissolved in tetrahydrofuran with a molar ratio of 1:2, and a solution 1 with a total concentration of 10mg / mL is prepared, and solution 1 is prepared with- Store at a temperature of 25°C for later use;

[0041] In step (2), tributyl borate is dissolved in ethyl acetate to prepare a solution 2 with a concentration of 20 mg / mL;

[0042] In step (3), both solution 1 and solution 2 are continuously injected into the inflow end of a flow chemical reaction tube with a diameter of 4mm at a flow rate of 1mL / min for reaction. The reaction time in the reaction tube is 20min, and the reaction temperature is 0°C ;

[0043]Step (4), in the outflow end of the flow chemical reaction tube, the reaction solution flowing out is mixed with a hydrochloric acid solution with a pH of 1 at a flow ratio of...

Embodiment 3

[0045] The only difference from Example 1 is that the total concentration of solution 1 in step (1) is 2 mg / mL, and the concentration of solution 2 in step (2) is 5 mg / mL.

[0046] In Example 3, the dibenzofuran-2-boronic acid product was obtained with a yield of 94.6% and a purity of 97.8%.

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Abstract

The invention relates to a preparation method of a heterocycle boric acid compound. The preparation method comprises the following steps: (1) preparing a halogenated heterocycle compound and triisobutyl aluminum into a solution 1; (2) preparing tributyl borate into a solution 2; (3) injecting the solution 1 and the solution 2 into an inflow end of a flowing chemical reaction tube for a reaction, wherein the reaction time in the reaction tube is 1 to 20 min, and the reaction temperature is 0 to 25 DEG C; and (4) mixing an effluent reaction solution and strong acid in a flow ratio of 1:(2-3) inside the inflow end of the flowing chemical reaction tube, mixing a mixed solution and water in the volume ratio of 1:(10-20), standing, collecting an obtained precipitate, and filtering, washing and drying the precipitate to obtain the heterocycle boric acid compound. The yield of the product can be increased to 95%, the purity of the product can be increased to 98.5%, moreover, the production energy consumption and danger can be further reduced, and the compound is more applicable for industrial large-scale production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of a heterocyclic boronic acid compound. Background technique [0002] Carbazole-2-boronic acid and dibenzofuran-2-boronic acid are intermediate reagents commonly used in organic chemical synthesis, and can be used to prepare a variety of chemical products with special functions. For example, carbazole-2-boronic acid can be used for The preparation of organic light-emitting diode (OLED) thin film displays has many advantages such as thinness, wide viewing angle, low power consumption, and fast response. Dibenzofuran-2-boronic acid can be used to prepare liquid crystal compounds, which are widely used in large display screens, portable In equipment such as computers and navigation systems, however, the preparation of carbazole-2-boronic acid and dibenzofuran-2-boronic acid is relatively difficult, and the common preparation method is by combining halogenated c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 谢应波张庆张华徐肖冰罗桂云张维燕
Owner 上海泰坦科技股份有限公司
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