Synlett 2004(4): 635-638  
DOI: 10.1055/s-2004-815445
LETTER
© Georg Thieme Verlag Stuttgart · New York

Selective Iodination of Alcohols with NaI/Amberlyst 15 in Acetonitrile

Mahmood Tajbakhsh*, Rahman Hosseinzadeh*, Zahra Lasemi
Department of Chemistry, Mazandaran University, Babolsar, Iran
Fax: +98(11252)42029; e-Mail: tajbaksh@umz.ac.ir;
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Publikationsverlauf

Received 15 September 2003
Publikationsdatum:
29. Januar 2004 (online)

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.

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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.