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新型多溴代水杨醛及其Schiff碱配体的合成与表征
引用本文:刘海彬,王梅.新型多溴代水杨醛及其Schiff碱配体的合成与表征[J].化学试剂,2010,32(2).
作者姓名:刘海彬  王梅
作者单位:1. 辽宁科技学院,生物医药与化学工程学院,辽宁,本溪,117004;大连理工大学,精细化工国家重点实验室,辽宁,大连,116012
2. 大连理工大学,精细化工国家重点实验室,辽宁,大连,116012
基金项目:国家自然科学基金资助项目 
摘    要:以芳基硼酸和3-溴-5-叔丁基水杨醛为原料,经Suzuki偶联反应分别得到3-苯基-5-叔丁基水杨醛和3-(4-甲基苯基)-5-叔丁基水杨醛。3-苯基-5-叔丁基水杨醛在溴化反应时,发现不同温度下反应结果不同:分别生成一溴代产物3-(4-溴苯基)-5-叔丁基水杨醛和二溴代产物3-(4-溴苯基)-5-溴水杨醛。在50℃下,3-(4-甲基苯基)-5-叔丁基水杨醛经溴化得到三溴代产物3-(4-甲基-3,5-二溴苯基)-5-溴水杨醛,再经过与(S)-缬氨醇缩合后得到手性Schiff碱配体。通过红外、高分辨质谱、核磁共振等手段对其结构进行了表征。

关 键 词:3-溴-5-叔丁基水杨醛  Suzuki偶联反应  溴化  Schiff碱

Synthesis and characterization of novel multi-brominated salicylaldehyde and its Schiff base ligand
LIU Hai-bin,WANG Mei.Synthesis and characterization of novel multi-brominated salicylaldehyde and its Schiff base ligand[J].Chemical Reagents,2010,32(2).
Authors:LIU Hai-bin  WANG Mei
Abstract:3-Phenyl-5-butylsalicylaldehyde and 3-(4-methyl_phenyl)-5-butylsalicylaldehyde were synthesized through the Suzuki coupling reactions using arylboric acids and 3-bromo-5-butylsalicylaldehyde as the starting materials.The products 3-(4-bromophenyl)-5-butylsalicylaldehyde with one bromine atom and 3-(4-bromophenyl)-5-bromosalicylaldehyde with two bromine atoms were obtained while 3-phenyl-5-butylsalicylaldehyde was brominated at different temperatures.3-(4-Methyl-3,5-dibromophenyl)-5-bromosalicylaldehyde with three bromine atoms was prepared when 3-(4-methylphenyl)-5-butylsalicylaldehyde was brominated at 50 ℃,then its chiral Schiff base ligand was obtained through condensation with(S)-valinol.The synthesized compounds were characterized by IR,HRMS,and NMR spectroscopy.
Keywords:3-bromo-5-butylsalicylaldehyde  Suzuki coupling reactions  bromination  Schiff base
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