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

2-benzyloxybenzonitrile compound and preparation method thereof

A technology of benzyloxybenzonitrile and nitrobenzonitrile, which is applied in the field of 2-benzyloxybenzonitrile compounds and their preparation, can solve the problems of no literature and publication, and achieve simple operation and mild reaction conditions Effect

Inactive Publication Date: 2017-02-22
XINYANG NORMAL UNIVERSITY
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, palladium-catalyzed o-nitrobenzonitrile and alcohol compounds directly through the denitration method to construct 2-benzyloxybenzonitrile compounds have no relevant literature and publications

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
  • 2-benzyloxybenzonitrile compound and preparation method thereof
  • 2-benzyloxybenzonitrile compound and preparation method thereof
  • 2-benzyloxybenzonitrile compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0029] A kind of preparation method of described 2-benzyloxybenzonitrile compound, comprises the following steps:

[0030] Alcohol with structure (I), o-nitrobenzonitrile compound of structure (II), catalyst Pd / TiO 2 And the base is dispersed in the solvent, and then by stirring and heating in the solvent, the 2-benzyloxybenzonitrile compound of the present invention with structure (III) can be obtained:

[0031]

[0032] Among them, R 1 Is aryl, substituted aryl; R 2 is fluorine, chlorine, methyl or methoxy.

[0033] The R 1 is aryl, and said aryl is phenyl, 2-thienyl, 2-furyl, 2-pyrrolyl or α-naphthyl;

[0034] The R 1 is a substituted aryl group, the substituted aryl group is 4-chlorophenyl, 4-fluorophenyl, 4-bromophenyl, 3-fluorophenyl, 3-chlorophenyl, 4-methylphenyl, 3 - methylphenyl, 3,4-dimethoxyphenyl, 4-methoxyphenyl;

[0035] The R 2 is 5-fluoro, 4-chloro, 5-methyl or 4-methoxy;

[0036] The alkali is potassium tert-butoxide, sodium tert-butoxide, sodium ...

Embodiment 1

[0044] In a clean and dry 20 ml Schlenk reaction tube, sequentially add 5% Pd / TiO 2 106 mg, 148 mg of o-nitrobenzonitrile, 162 mg of benzyl alcohol, 112 mg of potassium tert-butoxide, and then add 4 ml of toluene as a solvent, tighten the cap of the reaction tube to seal it, and react in an oil bath at 120°C for 20 Hour. After the reaction is finished, the mixture is centrifuged, and the obtained solid is the recovered palladium catalyst, which can be used to catalyze the reaction again after being dried. The centrifugate was directly spin-dried, dissolved in a small amount of dichloromethane, and separated through a silica gel column to obtain 156 mg of a light yellow solid.

[0045] The test data related to the product prepared in this example is: M.p.70-72°C; 1 H NMR (400MHz, CDCl 3 ): δ [ppm] = 7.62-7.24 (m, 7H), 7.07-6.70 (m, 2H), 5.15 (s, 2H); 13 C NMR (100MHz, CDCl 3 ): δ [ppm] = 160.3, 135.7, 134.5, 133.8, 128.9, 128.1, 127.0, 121.1, 116.4, 113.1, 102.5, 70.6. Th...

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 2-benzyloxybenzonitrile compound. The 2-benzyloxybenzonitrile compound has a specific structural formula shown in the description, wherein R1 is an aryl group or a substituted aryl group, R2 is fluoro, chloro, methyl group or methoxy group. The preparation method includes the steps of using alcohol and o-nitrobenzonitrile compounds as raw materials for a reaction; adding the corresponding base in the alcohol and the o-nitrobenzonitrile; conducting the reaction under the catalysis of heterogeneous catalyst Pd / TiO2 by heating in a solvent for a certain time to obtain the 2-benzyloxybenzonitrile compound. No oxidizing agent, reducing agent and metal ligand need to be added in the 2-benzyloxybenzonitrile compound, the reaction condition is mild, the operation is simple, and the catalyst can be recovered and recycled.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a 2-benzyloxybenzonitrile compound and a preparation method thereof. Background technique [0002] 2-benzyloxybenzonitrile compounds are a class of cyano-containing benzyl ether compounds, which widely appear in natural products, synthetic drugs and pesticides, and the cyano group it contains is a multifunctional functional group that can A variety of useful organic intermediates are synthesized through reactions such as hydration, reduction, and cycloaddition. Therefore, this type of compound is an important class of organic compounds. For example, existing patents disclose that such compounds have bactericidal effects (CN101875619A; IN2002MU01083). The synthesis methods of 2-benzyloxybenzonitrile compounds reported in previous literature mainly include: copper-catalyzed aryl halide and urea coupling reaction (Tetrahedron Lett.2013, 54, 5250); copper-catalyzed condensation of...

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): C07C253/30C07C255/54
CPCY02P20/584C07C253/30C07C255/54
Inventor 谭美容
Owner XINYANG NORMAL UNIVERSITY
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