Method for synthesizing bisdiboron

A technology of biboronic acid pinacol ester and pinacol, which is applied in the field of boron chemical synthesis, can solve problems such as inappropriateness, and achieve the effects of easy operation and reduced environmental hazards

Active Publication Date: 2014-11-19
CANGZHOU PURUI DONGFANG SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Method for synthesizing bisdiboron
  • Method for synthesizing bisdiboron
  • Method for synthesizing bisdiboron

Examples

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Embodiment 1

[0038] Synthesis of tri(tetrahydropyrrole) boron (1):

[0039] After argon replacement, add 110 kg of anhydrous toluene to the 500L enamel reaction kettle, cool the system down to -15°C, add triethylamine (80.9 kg, 800 moles) and tetrahydropyrrole (55.0 kg, 775 moles) , after stirring evenly, wait for dropwise addition. After argon replacement, add 20 kg of anhydrous toluene to another 200L enamel kettle, cool the system down to -15°C, add 62.6 kg of boron tribromide (250 moles), stir well and keep for 20-30 minutes. Under the protection of the argon system, slowly add the boron tribromide toluene solution into a 500L enamel reaction kettle. During the process of adding boron tribromide, the system begins to produce salt, and then gradually produces a large amount of solids.

[0040] The entire addition process takes about 6-8 hours, the temperature control should not exceed 0°C, and the stirring should be stable and uniform. After the addition is complete, keep stirring at ...

Embodiment 2

[0043] Synthesis of tri(tetrahydropyrrole) boron (1):

[0044] After nitrogen replacement, 130 kg of n-heptane was added to a 500L stainless steel reactor, the system was cooled to -15°C, triethylamine (83.5 kg, 825 moles) and tetrahydropyrrole (58.5 kg, 825 moles) were added, After stirring evenly, wait for dropwise addition. After nitrogen replacement, add 40 kg of n-heptane to another 200L stainless steel, cool the system down to -15°C, add 62.6 kg of boron tribromide (250 moles), stir well and keep for 20-30 minutes. Under the protection of the argon system, slowly add the boron tribromide toluene solution into a 500L enamel reaction kettle. During the process of adding boron tribromide, the system begins to produce salt, and then gradually produces a large amount of solids.

[0045] The entire addition process takes about 8-12 hours, the temperature control should not exceed 0°C, and the stirring should be stable and uniform. After the addition is complete, keep stirrin...

Embodiment 3

[0048] Synthesis of di(tetrahydropyrrole) boron bromide (2):

[0049] After nitrogen replacement, in the 500L enamel reaction kettle, add the toluene solution containing compound 1 (48.1 kg, 217 moles) in the first step, cool the system to -10 ° C, and add 27.1 kg of boron tribromide (108.5 moles, 0.5 equivalents) ) was added, stirred evenly and maintained for 20-30 minutes. The whole addition process takes about 3-5 hours, and the temperature control does not exceed 0°C. After the addition is complete, keep stirring at -10 to 0°C for 3 hours.

[0050] After the reaction, about 225 kilograms of the reaction solution was obtained, and the reaction yield of this step was 91%, which contained 68.4 kilograms of pure di(tetrahydropyrrole) boron bromide (2), which could directly enter the next step reaction. Analysis method: take the reaction solution and titrate it with silver nitrate solution. The pure product can take 200~500 milliliters of reaction liquids, the toluene rotary...

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Abstract

The invention relates to a method for synthesizing bisdiboron. The method comprises the following steps: preparing a tri-substituted boron midbody from raw materials, namely, nafoxidine and boron tribromide which are easy to obtain from the market, in the presence of an acid-binding agent triethylamine; subsequently reacting with boron tribromide to obtain a bromo-boron midbody; coupling the product in the presence of metal sodium to obtain nafoxidine-substituted coupled boron; finally adding pinacol to react, thereby obtaining a target product, namely, the bisdiboron. The method has the advantages that nafoxidine can be directly recycled, and the triethylamine hydrobromide can be also directly recycled after being simply neutralized and dried. The midbodies obtained in the method disclosed by the invention can be directly used after the solvent is simply distilled, except the compound, the midbodies are all solids when being purified, the operation is easy, the solvent and the reagents can be recycled, the damage to the environment is reduced, and the process can be successfully expanded to be the scale greater than 10kg.

Description

Technical field: [0001] The invention relates to a boron chemical synthesis method, in particular to a method for synthesizing biboronic acid pinacol ester. Background technique: [0002] In recent years, Suzuki coupling has been widely used in the synthesis of drugs and liquid crystal materials as an important means to realize the direct connection of carbon-carbon bonds. Among them, the preparation of organic boronic acid or borate compound as a coupling precursor has been extensively studied, and the methods are roughly divided into two categories: 1) the reaction of Grignard or lithium reagents with boron compounds; 2) the use of biboronic acid pinacol Esters couple directly with halides. The former is limited in scope of application due to the incompatibility of some groups with Grignard or lithium reagents. In order to reduce the formation of by-products, ultra-low temperature conditions are often required; in contrast, the latter uses metal palladium for coupling con...

Claims

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Application Information

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IPC IPC(8): C07F5/04
CPCY02P20/582
Inventor 冷延国桂迁张进余锦华
Owner CANGZHOU PURUI DONGFANG SCI & TECH
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