2,7-二溴螺[芴-9,9′-(2′,7′-二羟基-1′,8′-二磺酸基氧杂蒽)]的合成与表征  

Synthesis and Characterization of 2,7-Dibromospiro[Fluorene-9,9′-(2′,7′-Dihydroxy-1′,8′-Disulfonic-Xanthene)]

作　　者：汪凌云[1] 宋元杰[1] 曹德榕[1] 

机构地区：[1]华南理工大学化学与化工学院,广东广州510640

出　　处：《华南理工大学学报（自然科学版）》2010年第9期75-79,共5页Journal of South China University of Technology(Natural Science Edition)

基　　金：国家自然科学基金资助项目(20904010);华南理工大学中央高校基本科研业务费专项资金资助项目(2009ZM0170)

摘　　要：以芴为原料,经Br2/Fe溴代、CrO3/Ac2O氧化、间苯二酚/ZnCl2催化缩合得到2,7-二溴螺[芴-9,9′-(2′,7′-二羟基氧杂蒽)](Ⅲ),化合物Ⅲ经浓硫酸磺化合成目标产物2,7-二溴螺[芴-9,9′-(2′,7′-二羟基-1′,8′-二磺酸基氧杂蒽)](Ⅳ).考察了反应温度、反应物配比、反应时间等对磺化产物Ⅳ收率的影响,并通过傅里叶红外光谱、氢核磁共振谱、紫外?可见光谱等手段对化合物Ⅳ的结构进行了表征.确定了磺化反应的最佳条件,即反应温度70℃、每1g化合物Ⅲ对应加入浓硫酸3mL、反应时间2 h,该条件下磺化产物(化合物Ⅳ)收率达86.5%.First,2,7-dibromospiro[fluorene-9,9′-（2′,7′-dihydroxy-xanthene）]（Compound Ⅲ） was prepared through such three steps as Br2/Fe bromination,CrO3/Ac2O oxidation and resoreinol/ZnCl2 catalytic condensation,with fluorene as the starting material.Then,2,7-dibromospiro[fluorene-9,9′-（2′,7′-dihydroxy-1′,8′-disulfonic-xanthene）]（Compound Ⅳ） was synthesized via the sulfonation of Compound Ⅲ with concentrated sulfuric acid and was characterized by means of IR,1H NMR and UV-Vis,etc.Finally,the effects of reaction temperature,reactant molar ratio and reaction time on the sulfonation yield were investigated,and the optimal reaction conditions for Compound Ⅳwith a yield up to 86.5% were determined,that is,adding 1g of Compound Ⅲ together with 3mL concentrated sulfuric acid for the sulfonation at 70℃ for 2h.

关 键 词：芴 螺环 磺化 合成 产率 

分 类 号：O625.15[理学—有机化学]