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

Preparation method of 2-bromo-6-fluoronaphthalene

A technology of fluoronaphthalene and naphthylamine, which is applied in the field of pharmaceuticals, can solve problems such as equipment corrosion, unsuitability for the synthesis of 2-bromo-6-fluoronaphthalene, serious problems, etc., and achieve the effect of simple route

Inactive Publication Date: 2013-01-23
DATANGHANGZHOU PHARMACHEM
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this invention needs to be reacted at high temperature. Under the reaction conditions, the inorganic fluorides used are very corrosive to the equipment, so the requirements for the equipment are very strict.
In addition, what this method adopted is the nucleophilic substitution reaction on the aromatic ring, and when there is a more active bromine substituent on the 6-position, it is also prone to substitution, so it cannot be suitable for the synthesis of 2-bromo-6-fluoronaphthalene

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 2-bromo-6-fluoronaphthalene
  • Preparation method of 2-bromo-6-fluoronaphthalene
  • Preparation method of 2-bromo-6-fluoronaphthalene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Synthesis of 6-bromo-2-naphthylamine:

[0034] In a 2000ml three-necked flask equipped with a dropping funnel, a thermometer, a stirring device and a reflux condenser, add 1100ml of glacial acetic acid and 57.47g (0.25mol) of Turmeric's acid, start stirring, and heat to 70°C to dissolve the Turmeric's acid . 80 g (0.5 mol) of liquid bromine was added dropwise through the dropping funnel, and the temperature of the reactant was kept between 70-72° C. during the dropwise addition, and the dropwise addition was completed in about 1 hour. After the dropwise addition, the temperature was raised to reflux, and stirring was continued for 1.5 hours under reflux to complete the reaction. After the reaction finishes, the temperature of the reaction mixture is reduced to 65°C, adding 29.8g (0.251mol) metal tin powder and 340ml mass concentration is 35% hydrochloric acid, then the temperature of the reaction mixture is raised to reflux, and continues to stir for 2 Hour. Afte...

Embodiment 2

[0040] Carry out by the same method of embodiment 1, difference is that the thermal decomposition of the diazonium salt in the step (3) is carried out in the silicone oil that boiling point is in the range of 250-300 ℃, the product yield that obtains is 56.9%, HPLC The detection purity is 99.5%.

Embodiment 3

[0042] Carry out by the same method of embodiment 1, difference is, the thermal decomposition of the diazonium salt in the step (3) is carried out in liquid paraffin (C16-C20 normal alkanes), and the product yield that obtains is 58.4%, and HPLC detects 99.7% purity.

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

PropertyMeasurementUnit
thermal decomposition temperatureaaaaaaaaaa
Login to View More

Abstract

Disclosed is a process for preparing 2-bromo-6-fluoronaphthalene, wherein the raw material is a Tobias acid, and the product is obtained by bromating-debrominating, diazotizating, and thermal decomposing. The product obtained by the present process has high purity and stable quality. Moreover, in the present process, the route is simple, the reaction condition is mild, and there is no need for high pressure. Therefore, the process is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmacy and relates to a preparation method of 2-bromo-6-fluoronaphthalene. Background technique [0002] 2-Bromo-6-fluoronaphthalene is an intermediate for the synthesis of a class of niacin receptor competitive drugs. EP1809284 reported that this type of drug can be used to treat lipid abnormalities in patients with kidney disease, and can effectively reduce plasma low-density lipoprotein LDL, VLDL, At the same time, it increases the level of high-density lipoprotein HDL. Bioorganic & Medicinal Chemistry (2000), 8(8), 1925-1930 and (2005), 13(9), 3117-3126, Tetrahedron: Asymmetry (2002), 13(10), 1073-1081 and (2004), 15 (22), 3601-3608 reported a kind of pyrrole analgesics synthesized with 2-bromo-6-fluoronaphthalene as the basic raw material, which has a significant effect on the treatment of chronic pain. JP 2001019649 and EP 952135 (A1) reported a method for synthesizing liquid crystal active comp...

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 Patents(China)
IPC IPC(8): C07C25/22C07C17/00
CPCC07C2102/10C07C25/22C07C17/093C07C2602/10C07B39/00C07C17/00
Inventor 刘加庚林峰
Owner DATANGHANGZHOU PHARMACHEM
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