Réaction #43682

Équation de réaction

4-bromobenzo[b]thiophene

styrene

triethylamine

tris(2-methylphenyl)phosphine

→

title compound

4-[(E)-2-Phenylvinyl]benzo[b]thiophene

Solvants

diethyl ether

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed overnight under an argon atmosphere
2. 2
   Autrean insoluble material was removed by filtration
3. 3
   LavageThe filtrate washed with 1 mol/L hydrochloric acid, water and brine successively
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Autrethe solvent was removed under reduced pressure
6. 6
   AutreThe residue was purified by column chromatography on silica gel (eluent: n-hexane-n-hexane/ethyl acetate=5/1)

Mode opératoire

A mixture of 4-bromobenzo[b]thiophene (0.55 g), styrene (0.89 mL), triethylamine (1.81 mL), palladium(II) acetate (59 mg) and tris(2-methylphenyl)phosphine (0.16 g) in acetonitrile (10 mL) was refluxed overnight under an argon atmosphere. The reaction mixture was diluted with diethyl ether and an insoluble material was removed by filtration. The filtrate washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane-n-hexane/ethyl acetate=5/1) to give the title compound (0.56 g).

Source