Réaction #9761

Équation de réaction

tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane

intermediate 100

tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane

2-fluoro-4-bromobenzonitrile

trifuranyl phosphine

→

title compound

2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 3 hours
2. 2
   AutreThe solvent was removed
3. 3
   Autrethe residue purified by Biotage® chromatography
4. 4
   workup.ADDITIONa mixture of petroleum ether:ethyl acetate (4:1) as eluent

Mode opératoire

A mixture of tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane (intermediate 100, 0.037 g) and 2-fluoro-4-bromobenzonitrile (0.011 g) in tetrahydrofuran (2 ml) was treated with palladium bis(dibenzylideneacetone) (0.0035 g) and trifuranyl phosphine (0.0013 g) and the resulting mixture stirred at reflux for 3 hours. The solvent was removed and the residue purified by Biotage® chromatography using a mixture of petroleum ether:ethyl acetate (4:1) as eluent to give the title compound.

Source