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

HRID 15404

Reaktionsgleichung

Reaktionsgleichung von HRID 15404
Br[C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]1(/[CH:12]=[CH:11]/[C:2]2[C:10]3[CH:9]=[CH:8][S:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

8

Edukt 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 120942084-Bromobenzo[b]thiophene

Produkt 1

HCID 231567054-[(E)-2-Phenylvinyl]benzo[b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c9b724ccf96a4746a1af2ce58abf5586
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732596B2

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