2-溴-1,4,5-三甲氧基萘的简便合成

Facile Synthesis of 2-Bromo-1,4,5-trimethoxynaphthalene

目标化合物是合成具有抗癌、抗菌作用化合物的中间体,将通过简单易行的方法合成。以1,5-二羟基萘(Ⅰ)为起始原料,通过与乙酸酐进行酰化反应,得到1,5-二乙酰氧基萘(Ⅱ),再与N-溴代丁二酰亚胺、乙酸进行溴代、氧化反应得到2-溴-5-乙酰氧基-1,4-萘醌(Ⅲ),最后化合物Ⅲ与连二硫酸钠、氢氧化钾和硫酸二甲酯进行还原、水解和甲基化的"一步法"反应得到目标化合物,3步反应总产率为62%,中间体及目标化合物的结构均经IR、^(1)HNMR、^(13)CNMR和HRMS表征。

The target compound is a key intermediate in the synthesis of compounds with anti-cancer and anti-bacterial effects.A simple and easy method was used to successfully synthesize the target compound.1,5-Diacetoxynaphthalene(Ⅱ)was produced by acetylation reaction of 1,5-dihydroxynaphthalene(Ⅰ)with acetic anhydride.Subsequently,bromination and oxidation reaction of compoundⅡ,N-bromosuccinimide amine and acetic acid led to intermediate 5-acetoxy-2-bromo-1,4-naphthoquinone(Ⅲ).Finally,the target product was obtained via reduction,hydrolysis and methylation reaction of sodium dithionate,potassium hydroxide and dimethyl sulfate with intermediateⅢ.The total yield of the synthetic route was 62%.The structures of intermediates and target compound were characterized by IR,^(1)HNMR,^(13)CNMR and HRMS.