Benzofuran systems. Regioselective bromination and some other reactions of 1-(3-benzofuranyl)-2-phenylethanones

✍ Scribed by Halina Kwiecień; Ernst Baumann

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1998
• Tongue: English
• Weight: 218 KB
• Volume: 35
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570350647

✦ Synopsis

Abstract

1‐[3‐(2‐Alkylbenzofuranyl)]‐2‐(3,5‐dibromo‐4‐hydroxyphenyl)ethanones 5a,b and 1‐[3‐(2‐alkylbenzofuranyl)‐2‐(3‐bromo‐4‐methoxyphenyl)ethanones 3a,b were readily prepared by selective bromination of hydroxy 1a,b and methoxy 1c,d ethanones, respectively. A successful method of O‐alkylamination of 5a with N‐(2‐chloroethyl)‐N,N‐diethylammonium chloride to 6a by a two‐phase reaction under phase transfer conditions has been applied. Lithium aluminium hydride reduction of the carbonyl group of 1b to carbinol 4b was carried out in good yields.