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

Preparation method of 3, 5-difluorophenol

A technology of difluorophenol and difluorobromobenzene is applied in the field of preparation of compound 3,5-difluorophenol, can solve problems such as few synthetic routes, and achieve the effects of short steps and high yield

Pending Publication Date: 2021-05-11
HUNAN FURUI BIOPHARMA TECH CO LTD
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 3,5-difluorophenol has been increasingly used in various industries, but there are few published synthetic routes, so it is very promising to find an efficient and concise synthesis method for 3,5-difluorophenol

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 of 3, 5-difluorophenol
  • Preparation method of 3, 5-difluorophenol
  • Preparation method of 3, 5-difluorophenol

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0030] Its preparation method comprises the following steps:

[0031] Q1. Synthesis of 3,5-difluorophenylboronic acid: 3,5-difluorobromobenzene is used as raw material, and under the protection of an inert gas, a bromine extraction agent is added dropwise to extract bromine, and then reacted with boric acid to obtain 3,5-difluorobenzene boric acid.

[0032] Q2. Synthesis of 3,5-difluorophenol: Under suitable solvent conditions, 3,5-difluorophenylboronic acid is oxidized by an oxidant and catalyzed by iodine to obtain the final product 3,5-difluorophenol.

Embodiment 1

[0035] Synthesis of 3,5-difluorophenylboronic acid

[0036] Under nitrogen protection, 193g of 3,5-difluorobromobenzene was added to a 2L dry three-necked flask, and then 1000ml of anhydrous tetrahydrofuran was added as a solvent, the temperature was lowered to -70°C, and 320g of n-butyl Lithium, after the dropwise addition is completed, keep warm for 2 hours, then add 92g boric acid and keep warm for 1h, slowly rise to room temperature, and use TLC to determine the reaction end point. After the reaction was completed, filter and dry under reduced pressure to remove the residual solvent to obtain 124.1 g of 3,5-difluorophenylboronic acid with a yield of 78.5%.

Embodiment 2

[0038] Synthesis of 3,5-difluorophenylboronic acid

[0039] Under nitrogen protection, 193g of 3,5-difluorobromobenzene was added to a 2L dry three-necked flask, and then 1000ml of anhydrous tetrahydrofuran was added as a solvent, the temperature was lowered to -60°C, and 320g of n-butyl Lithium, after the dropwise addition is completed, keep warm for 2 hours, then add 92g boric acid and keep warm for 1h, slowly rise to room temperature, and use TLC to determine the reaction end point. After the reaction was completed, it was filtered and dried under reduced pressure to remove the residual solvent to obtain 135.6 g of 3,5-difluorophenylboronic acid with a yield of 85.8%.

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 provides a 3, 5-difluorophenol preparation method, which comprises the steps of S1, dissolving 3, 5-difluorobromobenzene in an organic solvent under inert gas protection, adding a bromine pulling agent to carry out a bromine pulling reaction, adding boric acid, filtering, and drying under reduced pressure to obtain 3, 5-difluorophenylboronic acid, and S2, dissolving the 3, 5-difluorophenylboronic acid, and adding an oxidizing agent and a catalyst to obtain the 3, 5-difluorophenol. The 3, 5-difluorophenol preparation method provided by the invention has the advantages of short steps and high yield, and is suitable for industrial production.

Description

Technical field [0001] The invention relates to the technical field of organic compound synthesis, and specifically relates to a preparation method of compound 3,5-difluorophenol. Background technique [0002] Organofluorine compounds are widely used in the pharmaceutical industry. About 15% to 20% of new drugs currently on the market each year are organofluorine compounds. [0003] In fluorine-containing drug molecules, the fluorine content is usually relatively low, and each fluorine atom or fluorine-containing group introduced has its specific purpose. The main effects of fluorine atoms on drug molecules are as follows: 1. The introduction of fluorine will not significantly change the three-dimensional configuration of the molecule, but will greatly change its electronic properties. 2. In the case of aromatic ring fluorination, ortho fluorination of π system and perfluoroalkyl chain, the introduction of fluorine is beneficial to the lipophilicity of the molecule. 3. Hig...

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
IPC IPC(8): C07C37/01C07C39/27
CPCC07C37/01C07F5/02C07C39/27
Inventor 鲁光英周跃辉
Owner HUNAN FURUI BIOPHARMA 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