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

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

Volume: 20 Issue: 10

Author(s): Shaojun Shan*, Xiumei Lian, Jingxuan Li and Wensen Zhong

Affiliation:

• School of Pharmaceutical and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan, 528458, P.R. China

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.

Cite this article as:

Shan Shaojun*, Lian Xiumei, Li Jingxuan and Zhong Wensen, First Synthesis of 2-Bromogentisyl Alcohol from Cultures of Penicillium Concentricum, Letters in Organic Chemistry 2023; 20 (10) . https://dx.doi.org/10.2174/1570178620666230315140839