4-羟基-3-异丁基苯硼酸的合成研究

Research on the synthesis of 4-hydroxy-3-isobutylphenylboronic acid

以5-溴-2-羟基苯甲醛(2)为起始原料,经苄基保护,与Wittig试剂反应,得关键中间体(4),(4)经格氏、酯化及水解反应,得4-苄氧基-3-异丁烯基苯硼酸(5),(5)经氢化还原反应,制得4-羟基-3-异丁基苯硼酸(1),总产率为63%。关键的中间体及产物的结构通过1H NMR、13C NMR和MS表征确认。

The route was started with 5-bromo-2-hydroxybenzaldehyde （2）, which was converted into the corresponding （4） by benzylation, followed by the reaction with Wittig reagent. 4-Benzyloxy-3-isobutenylphenylboronic acid（5 ）as synthesized by a three-step reaction of Grignard reaction and esterification and hydrolysis from （4）. The title compound （1） in overall yield of 63% was synthesized by the hydrogenation reduction reaction of （5）, and the structures of related intermediates and the product were characterized by 1H NMR,13C NMR and MS spectra.