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Bromination of 9 with 1.0 equiv of NBS in DMF afforded monobromide I in 93% yield, whereas bromination with 2.0 equiv of NBS yielded dibromide II in 97% yield. These results suggest relative reactivity of the pyrrole ring and the pendant aromatic ring against elecrophilic reagents.
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64
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DFT calculation of 22 indicated high atomic charge and extended HOMO at the C-1 position. The calculation suggested that electrophilic substitution reaction could occur at C-1 selectively. See Supporting Information.
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