Reaktion #312797

Reaktionsgleichung

5-(2,2-difluoro-vinyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

DMSO

water

potassium fluoride

→

title compound

Ausbeute 48.0%

5-(2,2,2-Trifluoro-ethyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl Ester

Ausbeute 48.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to room temperature
2. 2
   Waschenwashed sequentially with water and with brine
3. 3
   TrocknenThe organic phase was then dried over sodium sulfate
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Vorschrift

To a stirred solution of 0.71 mmol 5-(2,2-difluoro-vinyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester in 5 nml DMSO and 0.25 ml water was added 4.98 mmol potassium fluoride and the mixture was heated at 120° C. for 2 h. The mixture was cooled to room temperature and then taken up in THF and washed sequentially with water and with brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (48% yield). MS (m/e): 246.3 ([M+H−Me2C═CH2]+, 100%).

Quelle