Industrial production method of benzo [a] anthracene

Abstract

The invention discloses an industrial production method of benzo [a] anthracene, which belongs to the technical field of organic synthesis, and comprises the following steps of carrying out lithium substitution on 2-bromonaphthalene through 2, 2, 6, 6-tetramethylpiperidine lithium, and carrying out boron esterification and acidification through triisopropyl borate to obtain 2-bromo-3-naphthaleneboronic acid, carrying out Suzuki reaction on 2-bromo-3-naphthaleneboronic acid and iodobenzene to prepare 2-bromo-3-phenyl naphthalene, carrying out lithium substitution on 2-bromo-3-phenyl naphthalene and n-butyllithium, and preparing 2-formyl-3-phenyl naphthalene through DMF, carrying out Witting reaction on 2-formyl-3-phenyl naphthalene, chloromethyl ether triphenylphosphine salt and sodium tert-butoxide to prepare 2-methoxyvinyl-3-phenyl naphthalene, and enabling 2-methoxyvinyl-3-phenyl naphthalene to be subjected to ring closing through methanesulfonic acid, and preparing benzo [a] anthracene. Compared with an existing benzo [a] anthracene synthesis method, raw materials are cheap and easy to obtain, operation is easy, discharge of three wastes is small, preparation is environmentally friendly, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an industrial production method of benz[a]anthracene. Background technique [0002] Benzo[a]anthracene contains a strong active site, which can react with N-chlorosuccinimide, N-bromosuccinimide, dibromohydantoin, bromine, etc., and can be used in benzo[a] a] The corresponding halogenated substance is introduced into the 7-position of anthracene, and then other molecular fragments are introduced through Suzuki reaction, Buchwald reaction, Heck reaction and Ullmann reaction to realize the expansion of molecular structure. Benz[a]anthracene is used as a derivative synthesized as an intermediate, and is widely used in the synthesis of materials with conjugated structures, and has wide applications in fields such as field effect transistors and organic light emitting diodes. [0003] At present, the common synthesis method of benzo[a]anthracene uses 1-bromonaph...

AI Technical Summary

Problems solved by technology

The main problem with this method is that the three-step reactions all cause a large amount of waste water.

First step AlCl 3 Using 2.50eq, a large amount of high-salt wastewater containing aluminum is produced; the second step reaction temperature is lower than 90°C, the conversion is incomplete, and the temperature is higher than 120°C, a large amount of products are carbonized, and the reaction process requires at least 2 times the volume of methanesulfonic acid to do Solvent dehydration and ring closure, methanesulfonic acid cannot be recovered, resulting in more high-salt wastewater. During post-treatment, the emulsification is serious, and it is not easy to separate the phases. It takes a long time to stand still

The third step requires 10 times the volume of glacial acetic acid as a solvent. At least 5 eq of hydroiodic acid and 2.5 eq of hypophosphorous acid are used to hydrogenate benzo[a] anthracene, which causes a large amount of waste water

[0004] Generally speaking, emulsification often occurs in the washing process of the above preparation scheme, and the post-treatment operation is difficult, which leads to difficulty in reducing the cost of benz[a]anthracene and complicated operation

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