Reaktionsgleichung
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Mg]Br.Br[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.[Mg].Br[C:16]1[S:20][C:19]([C:21]2[S:22][C:23](Br)=[CH:24][CH:25]=2)=[CH:18][CH:17]=1>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:11]1[S:10][C:9]([C:16]2[S:20][C:19]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Thienylmagnesiumbromide, made from 13 gr (80 mmol) of T-Br and 2.43 gr (100 mmol) of magnesium in 50 ml of anhydrous ether, was added to a solution of 11.71 gr (36 mmol) of 5,5'-dibromo-2,2'-bithiophene and 100 mg (0.18 mmol) of Ni(dppp)Cl2 in 150 ml of ether. The reaction mixture was refluxed for 4 hours and subsequently poured on an ice/dilute hydrochloric acid mixture. The product was extracted with toluene and recrystallized from a mixture of toluene and ethanol. The resulting orange powder was dried in vacuo. Yield: 6,75 gr (20 mmol, 57%) of T4. M.p.: 203° C. (litt: 212). Elemental analysis: found% (theory%) C 56.49 (58.15), H 3.05 (3.05), S 37.0 (38.8). 1H-NMR (300 MHz, CDCl3): ∂=7.23 (2H, dd, J=5.0 and 1.0 Hz), ∂=7.19 (2H, dd, J=3.7 and 1.0 Hz), ∂=7.08 (4H, s), ∂=7.03 (2H, dd, J=5.0 and 3.7 Hz). M/z: 330 D (M.W.=330).
Aufarbeitung
- temperatureThe reaction mixture was refluxed for 4 hours
- extractionThe product was extracted with toluene
- customrecrystallized from a mixture of toluene and ethanol
- customThe resulting orange powder was dried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-5c36b1f41c744aadbd163bf24bf25ecd
- Quelldatensatz
- uspto-grants-1996_09
- Patentnummer
- US05556524
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