In a recent patent (US 6, 667, 303 B1 awarded to Wyeth), the synthesis of the br

Question

In a recent patent (US 6, 667, 303 B1 awarded to Wyeth), the synthesis of the brominated aromatic molecule 2 was described. This molecule serves as a key building block in new pharmaceuticals used to treat serotonin regulation. Gu, Y.; Pelletier, J. C. "Preparation of aryl substituted 1, 4-diazepanes as 5-HT2C receptor agonists." U.S. Patent 6667303, Wyeth (Madison, NJ), Dec. 23, 2003. This reaction is highly selective for the product shown. Briefly explain why each of these molecules might be disfavored relative to molecule 2. Mass Spectrometry Characterization. Describe how MS analysis could confirm the presence of a di-brominated analog (like molecule 7) in the crude reaction mixture. Give specific examples of observed peaks that would strongly suggest such a molecule was present.

Explanation / Answer

Presence of dibrominated analog can be confirmed by mass due to the presence of M, M+2 and M+4 peaks with the intensity rati 1:2:1.

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