9-菲硼酸的合成研究

Synthesis of 9-Phenanthreneboronic Acid

以9-溴菲为原料,采用格氏试剂法合成了9-菲硼酸。考察了亲核取代温度、反应原料配比以及反应时间等主要反应条件对合成反应收率的影响。采用高效液相色谱(HPLC)、傅立叶变换红外光谱(FTIR)、核磁(1HNMR)等方法对产品的结构和纯度进行了表征与分析。结果表明:合成9-菲硼酸的最佳工艺条件为:亲核取代温度为-40℃、反应物的摩尔配比为n(Mg):n(C14H9Br):n(B(OCH3)3)=1.1:1:1.5、9-溴菲的质量(g)与溶剂四氢呋喃(THF)的体积(mL)之比为1:7.5、亲核反应时间为3h。9-菲硼酸的收率最高可达71.24%,纯度可达99%。

9-Phenanthrenylboronic acid was synthesized by using 9-bromophenanthrene as the starting material, according to Grignard reagent method. The effects of reaction conditions such as the nucleophilic substitution temperature （T）, the reactant molar ratio, the ratio （R） of 9- bromophenanthrene （g） to THF （mL）, the reaction time （τ） on the reaction yield were investigated . The structure and purity of product was characterized and analyzed by HPLC, FTIR and ^1HNMR. The optimal reaction condition for the synthesis of 9-phenanthreneboronic acid was obtained as follows： T=-40℃, the molar ratio of n （Mg） ： n （Cl4H9Br） ： n （B （OCH3）3）=1.1 ： 1 ： 1.5, R =1 ： 7.5 and τ=3 h. Under the above reaction conditions, the yield of 9-phenanthreneboronic acid reached 71.24% and its purity was up to 99%.