2,6-二溴-1,4-萘醌的合成

Synthesis of 2,6-Dibromo-1,4-naphthoquinone

以6-溴-2-萘酚为原料,与三苯基二溴化膦进行定位取代反应,合成了2,6-二溴萘,再经CrO3/HOAc氧化得到了2,6-二溴-1,4-萘醌,此化合物鲜见报道,总收率23.6%。研究确定了2,6-二溴萘在CrO3/HOAc体系下氧化得到2,6-二溴-1,4-萘醌的最佳工艺条件为:n(三氧化铬)∶n(2,6-二溴萘)=3∶1,在100℃反应10 min,收率为78.0%。产物的结构经1H NMR、13C NMR、MS和HRMS分析表征。

A rarely reported compound 2,6-dibromo-1,4-naphthoquinone was synthesized with the total yield of 23.6% from the starting material 6-bromo-2-naphthol.Firstly,the bromination of 6-bromo-2-naphthol with triphenylphosphinedibromide afforded 2,6-dibromonaphthalene,and then was followed by the oxidation of 2,6-dibromonaphthalene with CrO_3 in glacial acetic acid.The optimum conditions of oxidation are as follows： the molar ratio of CrO_3 to 2,6-dibromonaphthalene is 3∶1,the reaction temperature is 100 ℃ and the reaction time is 10 min.The yield of 2,6-dibromo-1,4-naphthoquinone is 78.0%.The product was characterized by（）～1H NMR,（）～（13）C NMR,MS and HRMS.