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

Method for producing aromatic compound

A technology for aromatic compounds and manufacturing methods, which is applied in the field of cross-coupling reactions to manufacture aromatic compounds, can solve problems such as limitations and reaction substrate restrictions, and achieve excellent manufacturing processes, wide degrees of freedom/selection, and reduced environmental burdens Effect

Active Publication Date: 2018-05-11
TOSOH CORP +1
View PDF8 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the carbon-hydrogen activated cross-coupling reaction that does not require a halogen atom as a leaving group, although halogen wastes are not produced by-products, there are many restrictions on the reaction substrate, and there are problems that are still limited to limited molecular construction methods

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 producing aromatic compound
  • Method for producing aromatic compound
  • Method for producing aromatic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Add a stirring bar, 92 mg (0.60 mmol) of 4-nitroanisole, 110 mg (0.90 mmol) of phenylboronic acid, 9.1 mg (0.030 mmol) of palladium (II) acetylacetonate, and 2 -Dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropylbiphenyl 64mg (0.12mmol), tripotassium phosphate n-hydrate 480mg (1.8mmol), 18 -crown-616mg (0.060mmol), and 1,4-di Alkane 3mL. After the vial was tightly capped, it was heated and stirred at 130° C. for 24 hours. Next, the reaction solution was cooled to room temperature. Dichloromethane was added to the reaction liquid, and it was filtered through celite. The residue obtained by concentrating the filtrate was dissolved in diethyl ether (20 mL), and 30% aqueous hydrogen peroxide (5 mL) was added thereto. After stirring at room temperature for 1 hour, it was washed with distilled water (10 mL) and saturated aqueous iron(II) sulfate (10 mL). After extraction with diethyl ether (20 mL×3), the collected organic layer was washed with saturated brine (10 ...

Embodiment 2

[0061] Add a stirring bar, 119 mg (0.60 mmol) of 4-nitrobiphenyl, 110 mg (0.90 mmol) of phenylboronic acid, 9.1 mg (0.030 mmol) of palladium (II) acetylacetonate, and 2- Dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropylbiphenyl 64mg (0.12mmol), cesium fluoride 270mg (1.8mmol), and 1,4- two Alkane 3mL. After the vial was tightly capped, it was heated and stirred at 150° C. for 24 hours. Next, the reaction solution was cooled to room temperature. Dichloromethane was added to the reaction liquid, and it was filtered through celite. The residue obtained by concentrating the filtrate was dissolved in diethyl ether (20 mL), and 30% aqueous hydrogen peroxide (5 mL) was added thereto. After stirring at room temperature for 1 hour, it was washed with distilled water (10 mL) and saturated aqueous iron(II) sulfate (10 mL). After extraction with diethyl ether (20 mL×3), the collected organic layer was washed with saturated brine (10 mL). After drying with anhydrous magnesium...

Embodiment 3

[0065] Add a stir bar, 115 mg (0.60 mmol) of 4-(trifluoromethyl) nitrobenzene, 110 mg (0.90 mmol) of phenylboronic acid, and 9.1 mg (0.030 mmol), 2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropylbiphenyl 64mg (0.12mmol), cesium fluoride 270mg (1.8mmol), and 1,4-di Alkane 3mL. After the vial was tightly capped, it was heated and stirred at 130° C. for 24 hours. Next, the reaction solution was cooled to room temperature. Dichloromethane was added to the reaction liquid, and it was filtered through celite. The residue obtained by concentrating the filtrate was purified by medium-pressure column chromatography (using a Biotage SNAP Ultra column (particle size: 25 μm), developing solvent = hexane / ethyl acetate) to obtain the target 4-(trifluoromethyl Base) biphenyl 74mg (55% yield). pass 1 H and 13 C-NMR carried out the identification of the target substance.

[0066] 1 H-NMR(CDCL3)=δ7.70(s, 4H), 7.61(d, J=6.9Hz, 2H), 7.48(t, J=7.3Hz, 2H), 7.42(d, J=7.3Hz, 1H )...

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 method for producing an aromatic compound. In a cross coupling reaction, in a case where a halogen atom is selected as the leaving group of the raw material compound, a harmful halogen waste forms as a by-product after the reaction, and disposal process of the waste liquid is complicated and environmental burden is high. In a carbon-hydrogen activation cross coupling reaction which requires no halogen atom as the leaving group, although no halogen waste forms as a by-product, the reaction substrate is considerably restricted, and the reaction remains a limited molecular construction method. A method for producing an aromatic compound, which comprises subjecting an aromatic nitro compound and a boronic acid compound to a cross coupling reaction in the presence of ametal catalyst.

Description

technical field [0001] The present invention relates to a method for producing an aromatic compound, more specifically, to a method for producing an aromatic compound by cross-coupling reaction using an aromatic nitro compound and a boric acid compound as raw materials. Background technique [0002] Multi-substituted aromatic compounds have been widely used in the fields of medicine and pesticides, synthesis of natural products, liquid crystals and organic electroluminescent devices, and various methods have been developed as methods for their molecular skeleton construction. Among them, the synthesis reaction of coupling aromatic compounds using aromatic boronic acid derivatives (Suzuki cross-coupling reaction) is one of the particularly useful methods, and extensive improvements have been made (Non-Patent Document 1). [0003] Aromatic compounds having a leaving group are generally used as starting materials for the Suzuki cross-coupling reaction. As the leaving group, ha...

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 Applications(China)
IPC IPC(8): C07B37/00C07C41/30C07C43/205C07C43/225C07C43/20C07C1/32C07C15/14C07C15/24C07C15/28C07C17/263C07C22/08C07C25/18C07C67/343C07C69/78C07C69/92C07C69/76C07D213/16C07D213/127C07D295/023C07D295/033C07C45/68C07C47/575C07C49/784C07C49/84C07C315/04C07C317/14C07D213/64C07D215/06C07D217/02C07D409/04
CPCC07B37/00C07C1/321C07C17/263C07C41/30C07C45/68C07C67/343C07C315/04C07D213/127C07D213/16C07D213/64C07D215/06C07D217/02C07D295/023C07D295/033C07D409/04C07C2531/22C07C43/205C07C43/225C07C43/20C07C15/14C07C15/24C07C15/28C07C22/08C07C25/18C07C69/78C07C69/92C07C69/76C07C47/575C07C49/784C07C49/84C07C317/14C07C41/18C07B37/04C07C45/45C07C45/49C07C45/59C07C2603/24C07C1/323C07D217/04C07C25/13C07C69/94C07C49/78C07C45/61C07C67/28C07C303/30C07C2527/12
Inventor 江口久雄宫崎高则中尾佳亮
Owner TOSOH CORP
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