1-溴-6-氰基-2-萘酚的合成

Synthesis of 1-bromo-6-cyano-2-naphthol

摘要:

以2-萘酚（2）为原料，经一锅两步反应制备6-溴-2-萘酚（4），收率为89.0%；然后经氰化反应制备6-氰基-2-萘酚（5），投料比n(CuCN):n(4) = 1.5:1时收率为91.2%；最后分别用溴素和N-溴代丁二酰亚胺（NBS）两种不同的溴化试剂制备了1-溴-6-氰基-2-萘酚（1）。以溴素为溴化试剂，乙酸为溶剂，n(Br2)：n(5) = 1:1，1的收率为89.8%；该法成本较低，适合工业上大规模生产。以NBS为溴化试剂，乙腈为溶剂,n(NBS):n(5)=1.00:1.03 ，收率几乎定量（99.2%）；该法条件温和，简单高效，可避免溴素易挥发和吸入毒性大的缺点，更适合实验室小规模合成。

Abstract:

6-Bromo-2-naphthol (4) was prepared from 2-naphthol (2) via a two-step one-pot process in a yield of 89.0%; then 6-cyano-2-naphthol (5) was synthesized from 4 under the feeding ratio of n(CuCN):n(4)=1.5:1 in a yield of 91.2%. In the end, the bromination reagents Br2 and NBS were both adopted to prepare 1-bromo-6-cyano-2-naphthol (1) from 5. In the case of Br2 as bromination reagent, acetic acid as solvent, n(Br2):n(5) = 1:1, the yield is 89.8%；and this process is low-cost and suitable for industrialization. In the case of NBS as bromination reagent, acetonitrile as solvent, n(NBS):n(5)=1.00:1.03, the yield is 99.2%; this method is mild, simple, efficient for laboratory-scale preparation in which the problems of volatilization and high inhalation toxicity of Br2 are avoided.