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以1-溴萘为原料,合成了5-溴-7,7-二甲基-7H-苯并[C]芴,总产率为63.1%。其中,对中间体2-(1-萘基)苯甲醛、7-甲基-7H-苯并[C]芴和7,7-二甲基-7H-苯并[C]芴的合成工艺进行了优化。优化反应条件为:2-(1-萘基)苯甲醛合成中,催化剂Pd(dppf)Cl2质量分数3.0%,反应温度40℃,反应时间2 h,产率96.8%;7-甲基-7H-苯并[C]芴合成中,催化剂Amberlyst 15型离子交换树脂的质量分数0.6%,反应温度110℃,反应时间4 h,产率95.4%;7,7-二甲基-7H-苯并[C]芴合成中,n(对甲苯磺酸甲酯)∶n(7-甲基-7H-苯并[C]芴)=2.5∶1,反应温度40℃,产率91.0%。产品结构通过1HNMR和ESI-MS进行了表征。
Starting from 1-bromonaphthalene, 5-bromo-7,7-dimethyl-7H-benzo [C] fluorene was synthesized with the overall yield of 63.1%. Among them, the synthesis of intermediate 2- (1-naphthyl) benzaldehyde, 7-methyl-7H-benzo [C] fluorene and 7,7-dimethyl-7H-benzo [C] fluorene Optimized. The optimized reaction conditions were as follows: the mass fraction of Pd (dppf) Cl2 catalyst was 3.0%, the reaction temperature was 40 ℃, the reaction time was 2 h and the yield was 96.8% in 2- (1-naphthyl) -benzo [C] fluorene, the mass fraction of catalyst Amberlyst 15 ion exchange resin is 0.6%, the reaction temperature is 110 ℃, the reaction time is 4 h, the yield is 95.4%; the yield of 7,7-dimethyl-7H- [C] In the synthesis of fluorene, n (7-methyl-7H-benzo [C] fluorene) = 2.5: 1 was used as the n (ptoluenesulfonic acid methyl ester). The reaction temperature was 40 ° C and the yield was 91.0%. The product structure was characterized by 1H NMR and ESI-MS.