Reaction #43682

Reaction equation

4-bromobenzo[b]thiophene

styrene

triethylamine

tris(2-methylphenyl)phosphine

→

title compound

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

Solvents

diethyl ether

acetonitrile

Conditions

Workup

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

Procedure

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