Reaktion #2011551

Reaktionsgleichung

2-benzyl-4-bromoisoindoline

tributyl(vinyl)tin

→

2-benzyl-4-vinylisoindoline

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby bubbling nitrogen gas through the solution for 0.25 h
2. 2
   TemperaturThe contents of the reaction flask were cooled
3. 3
   Sonstigeevaporated
4. 4
   Wascheneluting with hexane/EtOAc 95/5
5. 5
   Sonstigeto give
6. 6
   Sonstigeafter evaporation the title compound as a pale oil that

Vorschrift

A solution of 2-benzyl-4-bromoisoindoline (16.7 g, 58.0 mmol) and tributyl(vinyl)tin (20.3 mL, 69.6 mmol) in toluene (400 mL) was degassed by bubbling nitrogen gas through the solution for 0.25 h. Tetrakis(triphenylphosphine)palladium(0) (1.30 g, 1.16 mmol) was added and the resulting solution heated in a 100° C. oil bath under nitrogen for 24 h. The contents of the reaction flask were cooled, evaporated and subjected to flash column chromatography eluting with hexane/EtOAc 95/5 to give after evaporation the title compound as a pale oil that turned pink on standing. LRMS (ESI) m/z 236 [(M+H)+; calcd for C17H18N: 236].

Quelle