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

Preparation method of 4-(3-fluorine benzyloxy) benzaldehyde

A technology of fluorobenzyloxy and p-hydroxybenzaldehyde, which is applied in the field of preparation of 4-benzaldehyde, can solve problems such as complex processing methods, difficult crystallization, and difficulty in industrialization, and achieve stable process, simple post-processing method, and simplified operation Effect

Inactive Publication Date: 2017-07-25
SHANDONG XINHUA PHARMA CO LTD
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (3) low yield, only 92.6%
[0007] (4) The post-treatment method is extremely complicated: 1) filter and wash to remove inorganic salts; 2) evaporate the solvent; 3) add water to dissolve, and extract with toluene; 4) evaporate toluene; 5) toluene / n-hexane recrystallization to obtain the target product
Especially when using a mixed solvent with low polarity as a heavy refining solvent, crystallization is difficult and oily matter is precipitated, which is difficult for industrialization

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 4-(3-fluorine benzyloxy) benzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 28.92g (200mmol) of compound II, 24.42g (200mmol) of compound III, 210mmol of potassium carbonate, and 150ml of acetonitrile, and heat up to reflux for 12h. The solvent was evaporated to obtain an oily product, which was added with 150 ml of water, stirred and cooled to crystallize, filtered at room temperature, and dried to obtain Compound I with a yield of 97.04% and an HPLC content of 99.53%.

[0027] The prepared compounds were tested, and the structural confirmation data are as follows:

[0028] MS(m / z): 231.0[M+H] + , 203.0[M-CO+H] +1 ;

[0029] HNMR: δ5.27(s, 2H), δ7.16(q, 3H), δ7.31(d, 2H), δ7.45(m, 1H), δ7.88(d, 2H), δ9.90 (s, 1H);

[0030] 13 CNMR: δ69.45(1C), δ114.94(1C), δ115.23(1C), δ115.38(2C), δ124.31(1C), δ130.63(1C), δ131.18(2C) , δ132.50 (1C), δ139.88 (1C), δ161.31 (1C), δ163.74 (1C), δ191.95 (1C).

Embodiment 2

[0032] Add 28.92g (200mmol) of compound II, 24.42g (200mmol) of compound III, 240mmol of sodium carbonate, and 290ml of acetonitrile, and heat up to reflux for 12 hours. The solvent was evaporated to obtain an oily product, which was added with 290 ml of water, stirred and cooled to crystallize, filtered at room temperature, and dried to obtain Compound I with a yield of 97.22% and an HPLC content of 99.47%.

Embodiment 3

[0034] Add 28.92g (200mmol) of compound II, 24.42g (200mmol) of compound III, 220mmol of sodium carbonate, and 250ml of acetonitrile, and heat up to reflux for 10h. The solvent was evaporated to obtain an oily substance, which was added with 250ml of water, stirred and cooled to crystallize, filtered at room temperature, and dried to obtain Compound I with a yield of 97.52% and an HPLC content of 99.55%.

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 belongs to the field of pharmaceutical chemistry, and particularly relates to a preparation method of 4-(3-fluorine benzyloxy) benzaldehyde. The preparation method comprises the following steps: adding fluorobenzyl chloride, p-hydroxy benzaldehyde, an acid-binding agent and acetonitrile into a reaction bottle, and performing heating reflux reaction; after the reaction is completed, boiling off the acetonitrile, and adding water for re-rectification, thus obtaining the 4-(3-fluorine benzyloxy) benzaldehyde. The acid-binding agent is potassium carbonate or sodium carbonate. According to the preparation method, no catalyst is added, so that use of sodium iodide or potassium iodide is avoided, and the cost is low; by the adoption of the inert solvent acetonitrile serving as a solvent, the reaction effect is unexpectedly good, and side reaction is less; water rectification can remove both inorganic salt and organic impurities; a post-treatment method is greatly simplified; the process is stable, easy to operate, high in operability and suitable for industrial production; the yield is 97.0 percent or above, and the HPLC content is up to 99.0 percent or above.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of 4-(3-fluorobenzyloxy)benzaldehyde. Background technique [0002] Safinamide was developed by Newron Pharmaceuticals to improve motor and cognitive function in people with Parkinson's disease. [0003] CN105061245A provides a method for preparing high-purity safinamide, and discloses the preparation of 4-(3-fluorobenzyloxy)benzaldehyde, the reaction of m-fluorochlorobenzyl (or m-fluorobromobenzyl) with p-hydroxybenzaldehyde, The reaction solvent is alcohols (methanol, ethanol, isopropanol) or toluene, the catalyst is sodium iodide, the post-treatment method: filter and wash to remove inorganic salts, evaporate the solvent, add water to dissolve and extract with toluene, evaporate toluene, toluene / n-hexane The target product was obtained by recrystallization of alkane with a yield of 92.6%. There are following disadvantages: [0004] (1) It ...

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): C07C45/64C07C47/575
CPCC07C45/64C07C47/575
Inventor 翟吉胜郑忠辉岳姗姗李程鹏徐玲
Owner SHANDONG XINHUA PHARMA 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