A. Grinev, S. A. Zotova, T. I. Mukhanova
Mar 1, 1982
Citations
0
Influential Citations
0
Citations
Journal
Pharmaceutical Chemistry Journal
Abstract
5(2-Phenylthiomethyl+3-carbethoxy-6-bromobenzofuryl)oxyacetic acid (IV) was prepared from the known 2-methyl-3-carbethoxy-5-hydroxy-6-bromobenzofuran [6]. Acylation of the last compound with acetic anhydride in the presence of triethylamine gave the 0-acetyl derivative (I). Bromination of I by N-bromosuccinimide (NBS) with illumination in the presence of benzoyl peroxide led to 2-bromoethyl-3-carbethoxy-5-acetoxy-6-bromobenzofuran (Ii). When the last compound was reacted with thiophenol in an acid medium, substitution of the bromine atom for the phenylthio residue and hydrolysis of the acetoxy group were observed; 2=phenylthiomethyl-3-carbethoxy-5-hydroxy-6-bromobenzofuran (III) was thus formed. Compound Iii was converted into a sodium derivative, which was successively treated by bromoacetic ester and aqueous alkali to form IV.