Réaction #3786

Équation de réaction

1,2-bis(5-bromo-2-methyl-3-thienyl)hexafluorocyclopentene

5-(5-trimethylsilyl-2-thienyl)-2-thienyl boric acid

potassium carbonate

→

hexafluorocyclopentene

Rendement 35.0%

Solvants

dimethoxyethane

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was refluxed for two hours
2. 2
   ConcentrationIt was then concentrated under reduced pressures
3. 3
   Extractionextracted with diethylether
4. 4
   Lavagerinsed with water
5. 5
   AutreWith the diethylether removed under reduced pressures
6. 6
   Autrethe product was purified by alumina column chromatogram

Mode opératoire

1,2-bis(5-bromo-2-methyl-3-thienyl)hexafluorocyclopentene (1.0 g, 0.002 mol) was dissolved in dimethoxyethane (50 ml), and palladium tetra(triphenylphosphine) (120 mg) was added to the mixture which was stirred for 5 minutes under argon atmosphere. With 5-(5-trimethylsilyl-2-thienyl)-2-thienyl boric acid (1.4 g, 0.006 mol) and an aqueous solution of potassium carbonate (0.1 mol dm-3, 10 ml) were added, the reaction mixture was refluxed for two hours. It was then concentrated under reduced pressures, extracted with diethylether and rinsed with water. With the diethylether removed under reduced pressures, the product was purified by alumina column chromatogram to give 1,2-bis[2-methyl-5{5-trimethylsilyl-2-thienyl)-2-thienyl}-3-thienyl]hexafluorocyclopentene (550 mg, 0.0007 mol).

Source