Process for preparing pentafluoropentanol

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

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C07C 3134

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060020539

ABSTRACT:
4,4,5,5,5-Pentafluoro-1-pentanol is prepared in a particularly advantageous manner from perfluoroethyl iodide by initially adding perfluoroethyl iodide in the presence of a radical initiator which does not carry any acyl groups to allyl alcohol and then hydrogenolytically dehalogenating the resulting 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol in the presence of a catalyst, an acid binder and a diluent.

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Kitazume, T and N Ishikawa. "Ultrasound-Promoted Selective Perfluoroalkylation on the Desired Position of Organic Molecules" J. Am. Chem. Soc. (1985) vol. 107, No. 18, pp. 5186-5191, published in US.
Larsson, U. "Synthesis of Amino Acids with Modified Principal Properties 1. Amino Acids with Fluorinated Side Chains" Acta Chemica Scandinavia (1993), vol. 47, pp. 380-390, published in Belgium.
Li, X et al., "Laboratory Scale Preparation of 4,4,5,5,5-Pentafluoropentan-1-thiol: An Important Chain of Anti-Breast Cancer Agents" Tetrahedron Letters (1994) vol. 35, No. 49, pp. 9141-9144, published in UK.
Park, JD et al. "Free-Radical Catalyzed Addition of Unsaturated Alcohols to Perhaloalkanes" J. Org. Chem. (Jun. 1961) vol. 26, pp. 2089-2095, published in US.

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