Synthesis method of 2-chloro-4-phenylbenzoquinazoline

Abstract

The invention discloses a synthesis method of 2-chloro-4-phenylbenzoquinazoline, and belongs to the field of organic chemical synthesis. In the synthesis method, 1-tetralone, benzaldehyde and urea areused as raw materials, and thereby the 2-chloro-4-phenylbenzoquinazoline is obtained through three steps of reaction of bigeminy reaction ring closing, oxidation and chlorination. The method has theadvantages of low requirements on equipment and reaction conditions, accessible raw materials, low cost and short process period, and can greatly enhance the synthesis efficiency and economic benefit.

Description

technical field [0001] The invention relates to a synthesis method of 2-chloro-4-phenylbenzoquinazoline, which belongs to the field of chemical synthesis. Background technique: [0002] 2-Chloro-4-phenylbenzoquinazoline is a fine chemical raw material widely used in the synthesis of heterocyclic compounds. It is also an important OLED intermediate discovered in recent years. 2-Chloro-4-phenyl As an OLED intermediate, phenylbenzoquinazoline has great market potential in the world, but the domestic production of such compounds is still relatively small. [0003] At present, the synthesis method of 2-chloro-4-phenylbenzoquinazoline can be roughly divided into two categories: (1) use 2-benzoyl-1-naphthol as a raw material for amination, ring closure, and three steps of chlorination The final product is obtained by the reaction, and the amination reaction will use expensive 2-bromoisobutyramide. In fact, the amination reaction includes two-step reactions of electrophilic substit...

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Problems solved by technology

[0002] 2-Chloro-4-phenylbenzoquinazoline is a fine chemical raw material widely used in the synthesis of heterocyclic compounds. It is also an important OLED intermediate discovered in recent years. 2-Chloro-4-phenyl As an OLED intermediate, phenylbenzoquinazoline has great market potential in the world, but domestic production of such compounds is still relatively small.

[0003] At present, the synthesis method of 2-chloro-4-phenylbenzoquinazoline can be roughly divided into two categories: (1) use 2-benzoyl-1-naphthol as a raw material for amination, ring closure, and three steps of chlorination The final product is obtained by the reaction, and the amination reaction will use expensive 2-bromoisobutyramide. In fact, the amination reaction includes two-step reactions of electrophilic substitution and rearrangement, and the reaction time is relatively long. The biggest problem is 2-benzyl The raw material of acyl-1-naphthol is difficult to obtain. The synthetic route uses naphthol and benzoyl to do the Fuckers acylation reaction, which will have a great probability of going to the para position of the hydroxyl group, and it is difficult to obtain the ortho product. The required reaction The conditions are relatively harsh, and post-treatment produces a large amount of acid water, and the yield is not high; (2) obtained by coupling 2,4-dichlorobenzo[h]quinazoline with phenylboronic acid or phenylboronic acid pinacol ester 2-Chloro-4-phenylbenzoquinazoline, yield 50~60%, 2,4-dichlorobenzo[h]quinazoline raw material is more expensive and difficult to obtain in this method, and needs to use palladium Catalyst, the production cost will be relatively high

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