Reaktion #312796

Reaktionsgleichung

triphenylphosphine

dibromodifluoromethane

5-formyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

→

title compound

Ausbeute 31.0%

5-(2,2-Difluoro-vinyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl Ester

Ausbeute 31.0%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at RT for 16
2. 2
   Einengenconcentrated in vacuo
3. 3
   SonstigeThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Vorschrift

To a stirred solution of 4.69 mmol triphenylphosphine in 5 ml DMF at 0° C. was added dropwise a solution of 4.69 mmol dibromodifluoromethane in 1 ml DMF and the mixture was stirred at RT for 30 min. 2.35 mmol 5-formyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester was then added at 0° C. and then 4.69 mmol zinc dust was added in small portions. The mixture was stirred at RT for 16 and then concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (31% yield). MS (m/e): 226.1 ([M+H−Me2C═CH2]+, 100%).

Quelle