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

A kind of method that adopts oxidative halogenation method to prepare haloaryl compound

A technology of halogenated aryl and compound, which is applied in the field of fine chemical synthesis to achieve the effects of good selectivity, mild reaction conditions and high yield

Inactive Publication Date: 2011-11-30
EAST CHINA NORMAL UNIV
View PDF1 Cites 15 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the solvents currently used for halogenation reactions are mainly volatile organic solvents

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
  • A kind of method that adopts oxidative halogenation method to prepare haloaryl compound
  • A kind of method that adopts oxidative halogenation method to prepare haloaryl compound
  • A kind of method that adopts oxidative halogenation method to prepare haloaryl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～6

[0012] Add 2 mmol catalyst, 5 mmol anisole, 10 mmol sodium bromide, 10 mmol hydrogen peroxide (30% aqueous solution) and 3 mL water into the round bottom flask, react for 3 hours at room temperature and constant speed, and then stand still , Extract twice with 15mL ether, combine the ether extracts, analyze with gas chromatography to determine the yield of bromoanisole; after gas chromatography analysis, the ether phase is saturated with NaHCO 3 The solution and water are washed separately, dried with anhydrous sodium sulfate, distilled to remove the ether, and then distilled under reduced pressure to obtain pure p-bromoanisole. The lower water phase (containing catalyst) can continue to be recycled. Table 1 shows the results of the aqueous oxidative bromination reaction of anisole and sodium bromide using different bifunctional imidazolium ionic liquids as catalysts.

[0013] Table 1 Aqueous oxidation bromination results of anisole and sodium bromide with different bifunctional...

Embodiment 7～15

[0020] Table 2 gives the catalyst 6 Under the action of, the oxidative halogenation reaction of different halogenated salts or halogen acids and anisole in the water phase results. Add 2 mmol catalyst 6 , 5 mmol anisole, 10 mmol halogenated salt (or halogen acid), 10 mmol hydrogen peroxide (30% aqueous solution) and 3 mL water were added to the round bottom flask, and the oxidation was carried out according to the steps and conditions of Examples 1 to 6. Halogenation reaction.

[0021] Table 2 catalyst 6 Aqueous oxidation and halogenation reaction results of different halogenated salts or halogen acids and anisole under action a

[0022]

[0023] a 2 mmol catalyst 6 , 5 mmol anisole, 10 mmol halogenated salt (or hydrohalic acid), 10 mmol hydrogen peroxide (30%), 3 mL water, room temperature, reaction time 3 hours.

[0024] b Gas chromatography analysis.

[0025]

Embodiment 16～30

[0027] Table 3 gives the catalyst 6 The oxidative bromination reaction results of hydrobromic acid and anisole in different ionic liquids under the action of. Add 0.5 mmol catalyst 6 , 5 mmol anisole, 5 mmol hydrobromic acid, 7.5 mmol hydrogen peroxide (30% aqueous solution) and 3 mL different ionic liquids were added to the round-bottom flask, and the oxidative bromination reaction was carried out according to the steps and conditions of Examples 1 to 6. .

[0028] table 3 catalyst 6 Oxidative bromination results of hydrobromic acid and anisole in different ionic liquids under action a

[0029]

[0030] a 0.5 mmol catalyst 6 , 5 mmol anisole, 5 mmol hydrobromic acid, 7.5 mmol hydrogen peroxide (30%), 3 mL ionic liquid, room temperature, reaction time 3 hours.

[0031] b Bmim=1-methyl-3-butylimidazole quaternary ammonium cation; Bpy=N-butylpyridine quaternary ammonium cation.

[0032] c OAc=Acetate, OTs=Toluenesulfonate, NTf 2 = Trifluoromethanesulfonimide anion.

[0033] d Gas c...

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 preparing halogenated aryl compounds through oxidation and halogenation. In the method, chlorine gas, bromine water or elementary iodine are prevented from serving as a halogenating agent, and in an aqueous phase or ionic liquid reaction medium, bidirectional ionic liquid is taken as a catalyst, hydrogen peroxide (commercial 30 percent aqueous solution) is taken as an oxidant, aryl compounds and halogeno salt (or haloid acid) are subjected to oxidation and halogenation to form the halogenated aryl compounds. The method is a green synthesis method; and the prepared halogenated aryl has high selectivity and yield, reaction conditions are mild, volatile organic solvents are not needed in the reaction, and the catalyst can be recycled.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and specifically relates to a new green synthesis method for preparing halogenated aryl compounds by using hydrogen peroxide as an oxidant to realize the catalyzed oxidation halogenation reaction of aryl compounds and halogenated salts. Background technique [0002] Halogenated aryl compounds are an important class of organic intermediates, which have very important uses in the synthesis of fine chemicals, medicine, pesticides and other industries, and are also necessary raw materials for various coupling reactions. With chlorine gas, bromine water or iodine element (Cl 2 、Br 2 or I 2 ) The electrophilic substitution reaction of aryl compounds for halogenating reagents is the most direct and commonly used method for synthesizing halogenating reagent compounds, but chlorine gas, bromine water or iodine as halogenating reagents are highly toxic, difficult to operate and use, and d...

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): C07B39/00C07C41/22C07C43/225C07C25/02C07C17/00C07C25/06C07C25/22C07C39/27C07C37/62C07C45/63C07C49/807C07C205/11C07C201/12
CPCY02P20/584
Inventor 刘晔王玲王洒洒路勇
Owner EAST CHINA NORMAL UNIV
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