Reaktion #3785

ord-a4ed8d077a2e4b55a7f88a3b17be86f8

Reaktionsgleichung

Cc1sc(Br)cc1C1=C(c2cc(Br)sc2C)C(F)(F)C(F)(F)C1(F)F
1,2-Bis(5-bromo-2-methyl-3-thienyl)hexafluorocyclopentene
COCCOC
dimethoxyethane
Cc1csc(OB(O)O)c1
4-methyl-2-thienyl boric acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
Cc1csc(-c2cc(C3=C(c4cc(-c5cc(C)cs5)sc4C)C(F)(F)C(F)(F)C3(F)F)c(C)s2)c1
1,2-bis[2-methyl-5-(4-methyl-2-thienyl)-3-thienyl]hexafluorocyclopentene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe reaction mixture was refluxed for two hours
  2. 2
    EinengenIt was then concentrated under reduced pressures
  3. 3
    Extraktionextracted with diethylether
  4. 4
    Waschenrinsed with water
  5. 5
    SonstigeWith the diethylether removed under reduced pressures
  6. 6
    Sonstigethe product was purified by alumina column chromatogram

Vorschrift

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 4-methyl-2-thienyl boric acid (852 mg, 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-(4-methyl-2-thienyl)-3-thienyl]hexafluorocyclopentene (447 mg, 0.0008 mol).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05734065uspto-grants-1998_03