摘要
通过改变反应物的投料比、溶剂、反应温度等因素高选择性合成了9,10-菲醌系列溴化物.结果表明:9,10-菲醌与N-溴代丁酰亚胺摩尔比为1.0∶1.4,在浓硫酸中0℃反应3 h得到了2-溴-9,10-菲醌,收率60%;在相同条件下,9,10-菲醌与N-溴代丁酰亚胺摩尔比为1.0∶2.3得到了2,7-二溴-9,10-菲醌,收率76%;9,10-菲醌与溴素摩尔比为1.0∶1.4,过氧化苯甲酰为引发剂,在冰乙酸中106℃反应3 h,得到了3-溴-9,10-菲醌,收率85%,在相同条件下,9,10-菲醌与溴素摩尔比为1.0∶3.4,得到了3,6-二溴-9,10-菲醌,收率90%.对9,10-菲醌的选择性溴化规律进行了探讨,发现溴化剂的加入量是决定生成单溴代或双溴代产物的主要因素.
A series of 9,10-phenanthrenequinone bromides were selectively synthesized by varying reaction conditions such as the molar ratio of reactants , the type of solvent and the reaction temperature .2-bromine-9,10-phenanthrenequinone was prepared by mixing 9,10-phednanthrenequinone with N-bromobutanimide in a molar ratio of 1.0∶1.4 at 0 ℃ for 3 h with concentrated sulfuric acid as solvent , and a 60%yield was obtained.Under similar condition, 76%yield of 2,7-dibromo-9,10-phenanthrenequinone was obtained with a molar ratio of 9, 10-phenanthrenequinone to N-bromobutanimide of 1.0∶2.3 at room temperature.85% yield of 3-bromine-9, 10-phenanthrenequinone was prepared by mixing 9, 10-phednanthrenequinone and bromine in a molar ratio of 1.0∶1.4 at 106 ℃for 3 h with acetic acid as solvent , and benzoyl peroxide as initiating agent .90%yield of 3,6-dibromo-9,10-phenanthrenequinone was obtained with the molar ratio of 9, 10-phenanthrenequinone to bromine of 1.0∶3.4 at the same condition. The selective bromination of 9, 10-phenanthrenequinone was discussed and it was found that the amount of brominating reagent was the major factor determining the production of monobromide or dibromide .
出处
《中南民族大学学报（自然科学版）》
CAS
北大核心
2016年第2期15-18,共4页
Journal of South-Central University for Nationalities：Natural Science Edition
基金
国家自然科学基金资助项目(21203253)
关键词
9
10-菲醌
菲醌溴代衍生物
溴化反应
溴化剂
选择性
9
10-phenanthrenequinone
bromo-derivation
bromination reaction
brominating agent
selective
