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Preparation method of 4-(9H-carbazol-9-yl)phenylboronic acid

A technology of phenylboronic acid and carbazole, which is applied in the field of preparation of 4-phenylboronic acid, can solve problems such as not being suitable for industrial production, and achieve the effect of avoiding ultra-low temperature reaction and being suitable for industrial production

Pending Publication Date: 2021-11-05
山东瑞辰新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented method uses different chemicals instead of traditional methods like boron trifluoride or lithography techniques that are less expensive than previous processes but still effective at producing certain types of compounds with specific properties such as fluorescence.

Problems solved by technology

The technical problem addressed by this patented technology relates to finding ways to make better quality chemicals from certain materials such as pigments or dyes without requiring extreme conditions during their synthesis processes.

Method used

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  • Preparation method of 4-(9H-carbazol-9-yl)phenylboronic acid

Examples

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Effect test

Embodiment 1

[0022] (1) Preparation of 9-(4-chlorophenyl)-9H-carbazole

[0023] Add 100g carbazole to a 1L three-necked flask, then add 500ml N,N-dimethylformamide, stir to dissolve; then add 137.4g 4-chlorobromobenzene, 206.6g potassium carbonate, 5.0g Pd(dppf) 2 Cl 2 , under the protection of nitrogen, the temperature was raised to 100°C for reaction, and after 8 hours TLC monitored the complete reaction of carbazole; after the reaction, the reaction solution was lowered to 25°C, filtered, and 500ml of water and 500ml of ethyl acetate were added to the filtrate to extract and separate the liquid; water The phase was extracted once more with 200ml ethyl acetate, and the organic phases were combined; the organic phase was washed 3 times with 500ml×3 saturated brine, dried over anhydrous sodium sulfate, and then evaporated to dryness to obtain a brown viscous substance; Add 800ml of toluene to the mixture, heat to reflux to dissolve, then evaporate 500ml of toluene under normal pressure, c...

Embodiment 2

[0030] (1) Preparation of 9-(4-chlorophenyl)-9H-carbazole

[0031] Add 2.00kg carbazole to a 20L glass kettle, then add 10L N,N-dimethylformamide, stir to dissolve; then add 3.43kg 4-chlorobromobenzene, 4.96g potassium carbonate, 100g Pd(dppf) 2 Cl 2 , under the protection of nitrogen, the temperature was raised to 100°C for reaction, and after 10 hours, TLC monitored the complete reaction of carbazole; after the reaction, the reaction solution was lowered to 25°C, filtered, and 10L of water and 10L of ethyl acetate were added to the filtrate for extraction and liquid separation; water The phase was extracted once more with 5L ethyl acetate, and the organic phases were combined; the organic phase was washed 3 times with 12L×3 saturated brine, dried over anhydrous sodium sulfate, and then evaporated to dryness to obtain a brown viscous substance; Add 11L of toluene to the mixture, heat to reflux to dissolve, then evaporate 4L of toluene under normal pressure, cool down to 0-10...

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Abstract

The invention relates to a preparation method of 4-(9H-carbazol-9-yl)phenylboronic acid, belonging to the technical field of organic synthesis. The preparation method comprises the following steps: with carbazole as an initial raw material, subjecting carbazole to reacting with 4-chlorobromobenzene to generate 9-(4-chlorphenyl)-9H-carbazole; and then condensing 9-(4-chlorphenyl)-9H-carbazole with triethyl borate, and carrying out hydrolyzing to generate the 4-(9H-carbazol-9-yl)phenylboronic acid. According to the method, n-butyllithium is not used in the process of preparing the 4-(9H-carbazol-9-yl)phenylboronic acid, so an ultralow-temperature reaction is avoided, and all the reactions are carried out under mild conditions; and compared with an existing synthesis process, the method is more suitable for industrial production.

Description

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Claims

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Application Information

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Owner 山东瑞辰新材料有限公司
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