Selective Iodination of Alcohols with NaI/Amberlyst 15 in Acetonitrile

Abstract

A simple and effective procedure for conversion of primary, secondary, allylic and benzylic alcohols into the corresponding iodides is described using NaI/Amberlyst 15 in acetonitrile at room temperature. Selective conversion of benzylic alcohols in the presence of saturated alcohols into the corresponding benzylic iodides is achieved under these conditions.

iodination - Amberlyst 15 - benzylic alcohol - saturated alcohol - iodides

References

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<A NAME="RD23203ST-24">24</A>

General Procedure for the Conversion of Alcohols to Iodides (Table 1). To a stirred suspension of alcohol (1 mmol) and NaI (0.150 g, 1 mmol) in MeCN (10 mL) was added amberlyst 15 (H⁺-form, 1 g), and the resulting mixture was stirred at r.t. After completion of the reaction (TLC or GC), Et₂O (10 mL) was added and washed with aq sat. NaHCO₃ solution, followed by NaHSO₄. The resultant organic layer was extracted with Et₂O (3 × 10 mL) and the combined extract dried over anhyd Na₂SO₄. The solvent was removed under reduced pressure to afford iodides in almost pure form. If necessary, products were purified by column chromatography (eluent: hexane-EtOAc). The products were identified by IR, ¹H NMR, and GC.

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