First Synthesis of 2-Bromogentisyl Alcohol from Cultures of Penicillium Concentricum

Abstract: The first synthesis of 2-bromogentisyl alcohol, a halogenated compound cytotoxicity to breast cancer cell line, was achieved in four steps. Key steps include (i) formylation of aromatic compound, (ii) bromination, (iii) demethylation and (iv) reduction. Compound 3 was prepared from 4- methoxyphenol (2) in 92% yield in the presence of MgCl2 and Et3N, then intermediate 4 was obtained by bromination of 3 in 78% yield. Subsequently, the direct demethylation of 4 with BBr3 afforded the intermediate 5 in 72% yield. Finally, title compound 1 was prepared by the reduction of 5 using NaBH4 in 87% yield. The overall yield is 45% from 4-methoxyphenol. This method is simple and the reaction conditions are mild.