Check patentability & draft patents in minutes with Patsnap Eureka AI!

Method for bromizing synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate

A technology of methoxyphenyl and ethyl acetate, which is applied in the field of bromination synthesis of 2-bromo-2-ethyl acetate, which can solve the threats of environmental protection, low total yield of synthetic routes, and increased industrial safety production, etc. problems, to achieve the effect of short production cycle, less "three wastes" and fewer reaction steps

Inactive Publication Date: 2019-05-28
安徽华胜医药科技有限公司
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the synthetic route reported in the above patent literature requires the use of highly toxic methanesulfonyl chloride, which is not only not environmentally friendly, but also highly toxic methanesulfonyl chloride increases the threat of industrial safety production
[0010] Simultaneously, the total yield of above-mentioned synthetic route is not high either

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
  • Method for bromizing synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate
  • Method for bromizing synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate
  • Method for bromizing synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A method for the synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate by bromination, the synthetic route is as follows:

[0028]

[0029] The method for the synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate by above-mentioned bromination comprises the following steps:

[0030] (1) Add the compound of formula II (1.0 g, 1.0 equiv.) into the reactor, add 15 mL of dichloromethane to dissolve and disperse, cool the reaction system to 0 ° C, and add 1.0 equiv. of triphenyl Phosphine and 1.0 equiv. of carbon tetrabromide, the reaction system was stirred at room temperature for 1 h;

[0031] (2) The reaction system is added to ice water, stirred, and the organic phase is separated. After the organic phase is washed with saturated brine, it is dried with sodium sulfate, and the solvent is recovered under reduced pressure. After column separation and purification, compound 2 as shown in formula I is obtained. -Ethyl bromo-2-(2-fluoro-3-methoxyphenyl...

Embodiment 2

[0033] A method for the synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate by bromination, the synthetic route is as follows:

[0034]

[0035] The method for the synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate by above-mentioned bromination comprises the following steps:

[0036] (1) Add the compound of formula II (1.0 g, 1 equiv.) into the reactor, add 10 mL of dichloromethane to dissolve and disperse, cool the reaction system to 0 ° C, and add 1.2 equiv. of triphenylphosphine based on the compound of formula II and 1.2 equiv. of carbon tetrabromide, the reaction system was stirred at room temperature for 3h;

[0037] (2) The reaction system is added to ice water, stirred, and the organic phase is separated. After the organic phase is washed with saturated brine, it is dried with sodium sulfate, and the solvent is recovered under reduced pressure. After column separation and purification, compound 2- Ethyl bromo-2-(2-fluoro-3-methoxyphenyl)ac...

Embodiment 3

[0039] A method for the synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate by bromination, the synthetic route is as follows:

[0040]

[0041] The method for the synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate by above-mentioned bromination comprises the following steps:

[0042] (1) Add the compound of formula II (1.2g, 1equiv.) into the reactor, add 13mL of dichloromethane, a mixed solvent of chloroform (the volume ratio of dichloromethane to chloroform is 1:1) to dissolve and disperse, and the reaction system cools down To 5°C, based on the compound of formula II, add 1.0 equiv. of triphenylphosphine and 1.0 equiv. of carbon tetrabromide, and stir the reaction system at room temperature for 2 hours;

[0043] (2) The reaction system is added to ice water, stirred, and the organic phase is separated. After the organic phase is washed with saturated brine, it is dried with sodium sulfate, and the solvent is recovered under reduced pressure. Aft...

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 method for bromizing synthesis of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate. The synthesis route is shown as followings (please see the specifications for the synthesis route). The synthesis method comprises the following steps: (1) 0.5-1.5 g of a 1 equiv. compound in a formula II is added into a reactor, 10-15 mL of an organic solvent is added for dissolving anddispersing, a reaction system is cooled to minus 5-5 DEG C, 1.0-1.2 equiv. triphenylphosphine and 1.0-1.2 equiv. carbon tetrabromide are added, and the reaction system is stirred for 1-3 h at the roomtemperature; and (2) the reaction system is added into ice water and stirred, an organic phase is separated, the organic phase is washed through a saturated salt solution and then dried through sodium sulfate, the solvent is subjected to decompression recovery, and after separation and purification, a compound, namely the 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate shown as a formula I isobtained.

Description

technical field [0001] The invention relates to the technical field of mechanical synthesis and pharmaceutical intermediates, in particular to a method for synthesizing 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate by bromination. Background technique [0002] Eagolix, whose structure is shown below, is clinically used for the treatment of uterine pain: [0003] [0004] 2-Bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate is a key intermediate for the synthesis of elagolix, and its structure is as follows: [0005] [0006] The patent number is: WO2009062087 discloses the synthesis method of this compound, the reaction process is as follows: [0007] [0008] In the technical scheme reported in this patent document, ethyl 2-(2-fluoro-3-methoxyphenyl)-2-hydroxyacetate is used as the starting material, and the target product. [0009] However, the synthetic route reported in the above-mentioned patent documents needs to use highly toxic methanesulfonyl chloride,...

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): C07C69/734C07C67/307
Inventor 胡志刚许良志何大荣杜小鹏钱祝进何勇陈越磊
Owner 安徽华胜医药科技有限公司
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com