Laboratory scale preparation of 4,4,5,5,5-pentafluoropentan-1-thiol: An important chain of antibreast cancer agents

Article abstract of DOI:10.1016/0040-4039(94)88448-X

Quantitative free radical addition of perfluoroethyl iodide to propargyl alcohol in the presence of sodium hydrosulfite gave E/Z-2-iodo-4,4,5,5,5-pentafluoro-2-penten-1-ols, which were converted to 4,4,5,5,5-pentafluoropentan-1-ol in one step in excellent yield by catalytic hydrogenation over platinum oxide in the presence of triethylamine. 4,4,5,5,5-Pentafluoropentan-1-thiol was obtained in good yield via modified Mitsunobu reaction of the alcohol.