Silicaphosphine (Silphos): a filterable reagent for the conversion of alcohols and thiols to alkyl bromides and iodides

Nasser Iranpoor*, Habib Firouzabadi*, Arezu Jamalian and Foad Kazemi

*Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran, Email: iranpoorchem.susc.ac.ir, firouzabadichem.susc.ac.ir

N. Iranpoor, H. Firouzabadi, A. Jamalian, F. Kazemi, Tetrahedron, 2005, 61, 5699-5704.

DOI: 10.1016/j.tet.2005.01.115

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Abstract

Silicaphosphine (Silphos), [P(Cl)_3−n(SiO₂)n] is a new heterogeneous reagent that converts alcohols and thiols to their corresponding bromides and iodides in the presence of molecular halogen in refluxing CH₃CN in high to quantitative yields. Separation of the Silphos oxide byproduct can be achieved by a simple filtration.

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Key Words

Silphos, Silicaphosphine, Alcohol, Thiol, Alkyl bromides, Benzyl bromides, Alkyl iodides, Benzyl iodides

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ID: J72-Y2005-2930