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

Reaction equation

FC(OC1C=CC(C=CC#N)=CC=1)CC(F)(F)F.F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.[F:28][C:29]([F:35])([CH:32]([F:34])[F:33])[CH2:30][OH:31]>>[F:28][C:29]([F:35])([CH:32]([F:34])[F:33])[CH2:30][O:31][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanol

HCID 145174-Fluorobenzonitrile

HCID 677248864-Tetrafluoropropoxycinnamonitrile

Product 1

HCID 290047704-(2,2,3,3-Tetrafluoropropoxy)benzonitrile

Procedure

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.