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Preparation method for N,N-bis (disubstituted benzene) amino benzaldehyde derivative

A technology of aminobenzene and derivatives, applied in the field of preparation of triphenylamine derivatives, can solve the problems of cumbersome routes, harsh conditions, high energy consumption, etc., and achieve good positioning effect

Active Publication Date: 2015-04-22
烟台九目化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has unavoidable shortcomings in industrial production: cyano compounds are used, which is highly toxic and pollutes the environment; and DIBAL is expensive, requires harsh conditions, low-temperature reaction, high energy consumption, and cumbersome routes, so it is not suitable for industrial applications.

Method used

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  • Preparation method for N,N-bis (disubstituted benzene) amino benzaldehyde derivative
  • Preparation method for N,N-bis (disubstituted benzene) amino benzaldehyde derivative
  • Preparation method for N,N-bis (disubstituted benzene) amino benzaldehyde derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Preparation of 4-(N,N-diphenylamino)benzaldehyde

[0025] 1, preparation of

[0026] Add 148g (0.8mol) of p-bromobenzaldehyde, 193.4g (3.12mol) of ethylene glycol, 69g (0.4mol) of p-toluenesulfonic acid, and 518g (445ml) of xylene into a 1000ml three-necked flask. Under nitrogen protection, stir and heat up to Water separation reaction at 100-110°C, after 8 hours of heat preservation, stop the reaction. Add 200 g of water, extract once with 300 g of toluene, combine the organic phases, wash with water until neutral, dry, and remove the solvent to obtain 171.6 g of crude product, which is recrystallized with 342 g of ethanol to obtain 155.8 g, yield: 85%, GC: 98.6%.

[0027] 2, preparation of

[0028] Add 25.4g (0.15mol) of diphenylamine, 34.4g (0.15mol) of m-bromobenzaldehyde ethylene acetal, 21.6g (0.225mol) of sodium tert-butoxide, 296g (344ml) of xylene into a 500ml three-necked flask, and blow nitrogen , add 0.3g (0.0015mol) of palladium acetate, 1....

Embodiment 2

[0033] Example 2 Preparation of 4-(N,N-bis(m-methylphenyl)amino)benzaldehyde

[0034] 1, preparation of

[0035] Add 185.6g (0.8mol) of p-iodoformaldehyde, 193.4g (3.12mol) of ethylene glycol, 69g (0.4mol) of p-toluenesulfonic acid, and 518g (445ml) of xylene into a 1000ml three-necked flask. Under nitrogen protection, stir and heat up to Water separation reaction at 100-110°C, after 8 hours of heat preservation, stop the reaction. Add 300 g of water, extract once with 300 g of toluene, combine the organic phases, wash with water until neutral, dry, and remove the solvent to obtain 220.8 g of crude product, add 342 g, and recrystallize with ethanol to obtain 183 g, yield: 83%, GC: 98.6%.

[0036] 2, preparation of

[0037] Add 29.6g (0.15mol) of dimethylaniline, 41.4g (0.15mol) of p-iodobenzaldehyde ethylene acetal, 21.6g (0.225mol) of sodium tert-butoxide, and 296g (344ml) of xylene into a 500ml three-necked flask , pass nitrogen, add 0.336g (0.0015mol) of palladium ac...

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Abstract

The invention relates to a preparation method for an N,N-bis (disubstituted benzene) amino benzaldehyde derivative. The preparation method comprises the following steps: halogenated benzene methylal is prepared through halogenated benzaldehyde, halogenated benzene methylal and N,N-bis (disubstituted phenyl) amine are subjected to the Buchwald coupling reaction, and the N,N-bis (disubstituted benzene) amino benzaldehyde derivative is obtained after acidation and dehydration are performed. The preparation method is suitable for preparing high-purity N,N-bis (disubstituted benzene) amino benzaldehyde derivatives, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of N,N-di(substituent phenyl)aminobenzaldehyde derivatives, belonging to the technical field of preparation of triphenylamine derivatives. Background technique [0002] N,N-bis(substituent phenyl)aminobenzaldehyde derivatives are important intermediates for the industrial preparation of other optoelectronic materials such as medicines and liquid crystals, and have broad market applications. Currently, such compounds are generally prepared by two methods. WO2010058995 discloses a method for preparing 4-(diphenylamino)benzaldehyde: triphenylamine, phosphorus oxychloride, and DMF are used as raw materials, and are prepared by Vilsmeier reaction. This method uses DMF and phosphorus oxychloride as raw materials, which is highly toxic and environmentally unfriendly; more importantly, due to the equivalence of the three benzene rings, a large amount of polyaldehyde-based impurities will be produced, which directl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C221/00C07C223/06
Inventor 宋有永程大兴胡晓腾和延岭李特
Owner 烟台九目化学股份有限公司