4-(7-溴苯并[c][1,2,5]噻二唑-4-基)-N,N-二苯基胺的合成

Synthesis of 4-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-N,N-diphenylaniline

报道一种荧光活性基团4-(7-溴苯并[c][1,2,5]噻二唑-4-基)-N,N-二苯基胺(1)的合成。以4,7-二溴苯并[c][1,2,5]噻二唑(2)和[4-(二苯基氨)苯基]硼酸(3)为原料,在四(三苯基膦)钯催化下发生Suzuki偶联反应得到目标化合物,产物结构经1H NMR、13C NMR和MS表征。并考察影响产物收率的主要因素,确定适宜的反应条件为:四(三苯基膦)钯为催化剂、物料比为n(3)∶n(2)=1.1∶1、反应溶剂为四氢呋喃与水的混合物(体积比为5∶1)、回流反应12h。在该最佳条件下,收率达到66.1%(以化合物2计)。

The synthesis of 4-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-N,N-diphenylaniline(1),a fluorescent active group,is reported.The target compound was synthesized from 4,7-dibromobenzo[c][1,2,5]thiadiazole(2)and(4-(diphenylamino)phenyl)boronic acid(3)by Suzuki coupling reaction catalyzed by tetrakis(triphenylphosphine)palladium.The structure of the product was characterized by1H NMR,13C NMR and MS.The main factors affecting the yield of the product(1)were also investigated,the appropriate reaction conditions were determined as follows:the tetrakis(triphenylphosphine)palladium was the catalyst,the ratio of materials was n(3)∶n(2)=1.1∶1,the reaction solvent was the mixture of tetrahydrofuran and water(the volume ratio was 5∶1),and the reaction was reflux for 12h.Under the optimum conditions,the product yield was up to 66.1%(calculated as compound 2).