In the metallation of 2-iodo-3-hydroxymethylquinoline(3) with BunLi(–78 °C), the halogen–metal exchange is shown to be faster than then the hydrogen (of the OH group)–metal exchange.
N. S. Narasimham and R. Ammanamanchi, J. Chem. Soc., Chem. Commun., 1985, 1368 DOI: 10.1039/C39850001368
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