3-甲氧基-2-羟基苯硼酸的合成与表征

摘要

Phenylboronic acid and its derivatives can be used for the detection and isolation of glucide and dopamine,which have been widely applied in chemistry,biology,and other fields.Using 2-methoxylphenol as a raw material,we synthesized 3-methoxyl-2-hydroxyl phenylboronic acid by a ortho-lithiation method including the three-step reaction of chloromethylation,boronic acidification,and hydrolyzation.Herein,ether linkage (-OMOM)was introduced by chloromethylation,which improved the electron supplying capacity of ortho-orientating group,thus effectively optimized reaction conditions of boronic acidification.The results of 1HNMR analysis, mass spectrometric analysis,and high performance liquid chromatography analysis show that the synthetic 3-methoxyl-2-hydroxyl phenylboronic acid has high purity and conforms to the molecular structure design.%苯硼酸及其衍生物可用于糖类、多巴胺等物质的检测和分离,广泛应用于化学、生物学等领域.采用邻位锂化法,以2-甲氧基苯酚为起始原料,通过氯甲基化、硼酸化和水解3步反应合成了3-甲氧基-2-羟基苯硼酸.其中,通过氯甲基化引入醚键(-OMOM),增强了邻位基团的供电子能力,改进了硼酸化的反应条件.核磁共振氢谱、质谱和高效液相色谱分析结果表明,合成的3-甲氧基-2-羟基苯硼酸纯度高,符合分子结构设计.