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

HRID 1376951Notes

Reaction equation

HRID 1376951 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:17])([CH:14]([F:16])[F:15])[CH2:12][OH:13].[H-].[Na+]>>[F:10][C:11]([F:17])([CH:14]([F:16])[F:15])[CH2:12][O:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydride

Product 1

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

Procedure

In a first step, p-chlorobenzonitrile is reacted with 2,2,3,3-tetrafluoropropanol in the presence of bases, for example sodium hydride, with exchange of the p-chlorine atom to give 4-(2,2,3,3-tetrafluoropropoxy)benzonitrile. The second step is to reduce the 4-(2,2,3,3-tetrafluoropropoxy)benzonitrile by metal hydrides, for example diisobutylaluminum hydride, 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde being formed. The 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde is reacted stereoselectively with ethyl diethylphosphonoacetate in a third reaction step to give ethyl (E)-4-(2,2,3,3-tetrafluoropropoxy)cinnamate.

Sources & evidence

ORD record
ord-a06724dfea8d4a8aaed51fc2d7d0f40f
Source dataset
uspto-grants-1997_09
Patent number
US05663410

Reaction notes

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