直接碘化反应高效合成碘代芳烃
Efficient Synthesis of Iodide-substituted Aromatics by Direct Iodination
投稿时间:2017-11-07  修订日期:2018-01-13
DOI:
中文关键词: 碘代芳烃  3-叔丁基水杨醛  3-叔丁基-5-碘水杨醛  碘化反应  合成
英文关键词: Iodide-substituted aromatics  3-tert-butylsalicylaldehyde  3-tert-butyl-5-iodosalicylaldehyde  iodination  synthesis
基金项目:国家自然科学基金项目(面上项目,重点项目,重大项目)
作者单位E-mail
谢光勇 中南民族大学 催化材料科学国家民委-教育部暨湖北省重点实验室 xiegy@scuec.edu.cn 
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中文摘要:
      碘代芳烃是重要的有机合成中间体. 本文以3-叔丁基水杨醛为原料,分别通过三种碘化方法合成3-叔丁基-5-碘水杨醛,比较三种方法的优劣,提出了一种以水-乙醇为溶剂、KI为碘试剂、H2O2为氧化剂制备3-叔丁基-5-碘水杨醛的有效合成方法; 确定了碘取代反应的最佳条件为: 水-乙醇体积比为3:1,H2SO4质量与溶剂体积比为2.5g /40ml,反应物-碘化钾-氧化剂摩尔比为1:1:2,反应温度为70℃,反应时间为6h;在此条件下3-叔丁基-5碘水杨醛摩尔收率高达88.1%;应用该方法成功使2,6-二氟苯胺和2,6-二异丙基苯胺进行碘化反应,产物摩尔收率分别可达87.3%和85.6%.
英文摘要:
      3-tert-butyl-5-iodosalicylaldehyde was synthesized through three iodide methods using 3-tert-butylsalicylaldehyde as starting material. By comparing the three methods, a new method for the efficient synthesis of 3-tert-butyl-5-iodosalicylaldehyde was proposed under mild conditions by using water-ethanol as solvent, potassium iodide as iodine reagent and hydrogen peroxide as oxidant The results indicated that the optimum reaction conditions were as follows: the volume ratio of water to ethanol of 3︰1, the mass concentration of sulfuric acid of 62.5 mg/mL, molar ratio of reactant/potassium iodide/oxidant of 1︰1︰2, reaction temperature of 70 ℃ and reaction time of 6 h. Under these conditions, the yield of 3-tert-butyl-5-iodosalicylaldehyde could reach 88.1%. Furthermore, iodination of 2,6-difluoroaniline and 2,6-diisopropylaniline to corresponding iodide-substituted products can also be performed through this method with 87.3% and 85.6% of yields, respectively.
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