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Brominated Oxymorphone Impurities: Regioselective Synthesis & Characterization of 1-Bromo- & 2-Bromoxymorphone

Authors: Elizabeth Marek PhD, Gregory Kirkovits PhD, Huahua Jian PhD, Uma Sreenivasan PhD
Presented at AAPS, November 2009

Abstract
The use of synthetic opiate impurities as reference materials has become vital to the pharmaceutical industry. To this end, brominated Oxymorphone impurities 1-bromooxymorphone (1) and 2-bromooxymorphone (2) were synthesized using desirable short, direct, and Regioselective methods. Using a combination of 1H, 13C and 2-D NMR spectra, unequivocal evidence for the electrophilic aromatic substitution of brominates at the 1- and 2-positions of the aromatic ring of Oxymorphone has been demonstrated.

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