An Expedient Large-Scale Preparation of a Dibenz[b,e]oxepinone Derivative

Abstract

A convenient, large-scale synthesis of a dibenz[b,e]oxepinone derivative is described. The dibenz[b, e]oxepinone ring system is constructed using an iron chloride catalyzed intramolecular Friedel-Crafts cyclization of an appropriate phenoxymethylbenzoic acid chloride in toluene, reagents and conditions that are economically and environmentally compatible with large-scale preparation.

^† Present Address: Department of Medicinal Chemistry, Merck Research Laboratories, West Point, PA 19486

^† Present Address: American Cyanamid Company, Agricultural Products Research Division, P.O. Box 400, Princeton, NJ 08543 - 0400

Notes

^† Present Address: Department of Medicinal Chemistry, Merck Research Laboratories, West Point, PA 19486

^† Present Address: American Cyanamid Company, Agricultural Products Research Division, P.O. Box 400, Princeton, NJ 08543 - 0400

HPLC analysis of the reaction mixture showed that it is a mixture of diester (3) and the two half-acid/ester (4) and (5).