2,2,3,3-Tetrafluoro-1-propanol → 4-(2,2,3,3-Tetrafluoropropoxy)benzonitrile

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Reaction Steps

According to Ann. N.Y. Acad. Sci (1988), 544, pages 86 to 100 (Chem. Abstr. 111, 208650), 4-tetrafluoropropoxycinnamonitrile can be prepared in the following manner. 4-Fluorobenzonitrile is reacted with 2,2,3,3-tetrafluoropropanol to give 4-(2,2,3,3-tetrafluoropropoxy)benzonitrile which is then reduced by complex hydrides to give 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde. The 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde leads to the 4-tetrafluoropropoxycinnamonitrile by reaction with the anion of diethyl cyanomethylphosphonate in the context of a Wittig-Horner reaction.

Provenance & Evidence