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Abstract

Organic halides are important synthetic intermediates in numerous reactions. They are also important due to the variety of radiohalogen-containing pharmaceuticals that have been developed in recent years [1–3]. The trialkylboranes prepared via hydroboration are conveniently converted to alkyl halides when 1 equiv of sodium hydroxide or sodium methoxide in methanol is added to a mixture of 1 mol of organoborane and 1 mol of iodine. The reaction becomes instantaneous and affords the corresponding alkyl halides. A second mole of iodine and base react similarly (Eq. 13.1) [4–6], but the third alkyl resists the reaction under these conditions.

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Section 13.1

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(2007). Synthesis of Halides. In: Hydroboration and Organic Synthesis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49076-0_13

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