Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method for 3-carboxyphenylboronic acid

A technology of carboxyphenylboronic acid and methylbenzeneboronic acid, which is applied in the field of preparation of 3-carboxyphenylboronic acid, can solve the problems of unsuitability for industrial production and high cost of raw materials, and achieve the effects of low cost, simple operation, and avoiding high-temperature reactions

Inactive Publication Date: 2017-07-14
BENGBU CHINA SYNCHEM TECH CO LTD
View PDF2 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The existing synthetic method is to use 3-cyanophenylboronic acid to obtain 3-carboxyphenylboronic acid after hydrolysis. Although this method only needs one step, the cost of raw materials is high, and it is not suitable for industrial production. Although the present invention has two steps, the reaction raw materials are easy to obtain , simple process, easy post-processing, mild conditions, low reaction cost, little environmental pollution, high product yield, good quality and suitable for industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method for 3-carboxyphenylboronic acid
  • Preparation method for 3-carboxyphenylboronic acid
  • Preparation method for 3-carboxyphenylboronic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 0.05mol (0.1eq) m-bromotoluene, 0.55mol (1.1eq) magnesium chips, several grains of elemental iodine, 300ml THF into the reaction flask, stir, heat up to reflux, Grignard triggers, continue to drop m-bromotoluene under reflux 0.45 mol (0.9 eq). After the dropwise addition, reflux and heat preservation reaction, when the reaction time is up, lower the temperature to -60.0°C, start to add 1.0mol (2.0eq) of trimethyl borate dropwise, after the dropwise addition is complete, keep the heat preservation reaction until the raw materials are reacted, heat up, add water, and dropwise add hydrochloric acid Hydrolyze, adjust the pH to 1-2, heat preservation reaction, the reaction time is up, rotary evaporation, draining, beating and purification, drying to obtain 0.44mol of white solid 3-methylphenylboronic acid, moisture 0.05%, purity 98.64%, yield is 88.0%.

[0025] Drop into 120ml of aqueous sodium hydroxide solution (30%) in the reaction flask, 0.44mol of the above-mention...

Embodiment 2

[0027] Add 0.10mol (0.1eq) m-bromotoluene, 1.1mol (1.1eq) magnesium chips, a few grains of elemental iodine, 800mlTHF into the reaction flask, stir, heat up to reflux, Grignard triggers, and continue to drop m-bromotoluene 0.90ml under the reflux state. mol (0.9eq), after the dropwise addition, reflux and keep warm for reaction, when the reaction time is up, cool down to -50.0°C, start to add 2.2mol (2.2eq) of trimethyl borate dropwise, after the dropwise addition is complete, keep warm for reaction until the raw materials are reacted, then raise the temperature , add water, add hydrochloric acid dropwise for hydrolysis, adjust pH to 1-2, keep warm for reaction, when the reaction time is up, rotary evaporate, drain, beat and purify, and dry to obtain 0.90mol of white solid 3-methylphenylboronic acid, moisture 0.03%, purity 98.86%, yield 90.0%.

[0028] Drop into 250ml of aqueous sodium hydroxide solution (30%) in the reaction bottle, 0.90mol of the above-mentioned 3-methylphen...

Embodiment 3

[0030] Add 0.10mol (0.1eq) m-bromotoluene, 1.2mol (1.2eq) magnesium chips, several grains of elemental iodine, 800mlTHF into the reaction flask, stir, heat up to reflux, Grignard triggers, and continue to drop m-bromotoluene 0.90ml in the reflux state. mol (0.9eq), after the dropwise addition, reflux and keep warm for reaction, when the reaction time is up, cool down to -60.0°C, start to add 2.0mol (2.0eq) of trimethyl borate dropwise, after the dropwise addition is complete, keep warm for reaction until the raw materials are reacted, then raise the temperature , add water, add hydrochloric acid dropwise for hydrolysis, adjust pH to 1-2, keep warm for reaction, when the reaction time is up, rotary evaporate, drain, beat and purify, and dry to obtain 0.87mol of white solid 3-methylphenylboronic acid, moisture 0.03%, purity 98.57%, and the yield was 87.0%.

[0031] Drop into 300ml of aqueous sodium hydroxide solution (30%) in the reaction flask, 0.87mol of the above-mentioned 3-...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method for 3-carboxyphenylboronic acid, relating to the technical field of organic synthesis. The preparation method comprises the steps of performing Grignard reaction on m-bromomethyl benzene, magnesium scraps and iodine by using the m-bromomethyl benzene as a starting material, so as to generate a Grignard reagent, performing boronated reaction on the Grignard reagent and trimethyl borate so as to prepare 3-Tolylboronic acid, and oxidizing the 3-Tolylboronic acid with potassium permanganate in an alkaline condition so as to prepare 3-carboxyphenylboronic acid. According to the preparation method, cheap m-bromomethyl benzene easy to obtain is used as the starting material, the 3-carboxyphenylboronic acid is prepared through Grignard reaction, boronated reaction and oxidization reaction, the operations are simple, the average purity of the product 3-carboxyphenylboronic acid reaches 99.3%, and the average total yield reaches 50%. The product yield and purity are ensured at low cost, so that the preparation method is applicable to industrial production.

Description

[0001] Technical field: [0002] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3-carboxyphenylboronic acid. [0003] Background technique: [0004] 3-Carboxyphenylboronic acid is an important intermediate in organic synthesis. It can be used in the synthesis of many natural products and organic materials to synthesize polyenes, styrene and biphenyl derivatives through suzuki aryl coupling reaction. [0005] The existing synthetic method is to use 3-cyanophenylboronic acid to obtain 3-carboxyphenylboronic acid after hydrolysis. Although this method only needs one step, the cost of raw materials is high, and it is not suitable for industrial production. Although the present invention has two steps, the reaction raw materials are easy to obtain , simple process, easy post-treatment, mild conditions, low reaction cost, little environmental pollution, high product yield, good quality and suitable for industrial production...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 杨青赵士民徐剑霄王庆强
Owner BENGBU CHINA SYNCHEM TECH CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com