Nitrogen → 3,3'''-Dihexyl-2,2':5',2'':5'',2'''-quaterthiophene

HRID 254119

Reaktionsgleichung

Reaktionsgleichung von HRID 254119
Br[C:2]1[S:6][C:5]([C:7]2[S:8][C:9](Br)=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.N#N.[NH4+].[Cl-].C(O[CH2:20][CH3:21])C>>[CH2:20]([C:4]1[CH:3]=[CH:2][S:6][C:5]=1[C:7]1[S:8][C:9]([C:9]2[S:8][C:7]([C:5]3[S:6][CH:2]=[CH:3][C:4]=3[CH2:9][CH2:10][CH2:11][CH2:7][CH2:20][CH3:21])=[CH:11][CH:10]=2)=[CH:10][CH:11]=1)[CH2:21][CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 4

HCID 947NitrogenHCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 6389085,5'-Dibromo-2,2'-bithiophene

Produkt 1

HCID 121416303,3'''-Dihexyl-2,2':5',2'':5'',2'''-quaterthiophene

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

The Grignard reagent prepared above, added dropwise to a suspension of 5.0 g (15.4 mmoles) of 5,5′-dibromo-2,2′-bithiophene and 0.084 g (0.154 mmoles) of Ni(dppp)2Cl2 in 50 mL dry ethyl ether. Typically, the Grignard is added from a feeding funnel under an inert gas (e.g., N2). The resulting mixture was heated to reflux for about 20 hours. The resulting mixture is cooled to about room temperature (e.g., to about 20° C.) and combined with about 200 mL of 5% aqueous NH4Cl to which some ice is added, to effect hydrolysis. The aqueous phase is extracted with about 2×100 mL of CH2Cl2. The organic phases combined are back washed with about 200 mL water and dried over MgSO4. The solvent is evaporated to give a raw product, 3,3′″-dihexyl-[2,2′;5′,2″;5″,2′″]quaterthiophene, which can be purified using, for example, a silica-gel column using hexanes 100% as eluant to give 6.4 g of material, (yield=83.4%). Proton NMR can be used to determine the presence of the raw product: 1HNMR: 7.25 ppm, (2H, d), 7.20 ppm, (2H, d), 7.10 ppm, (2H, d), 7.00 ppm, (2H, d), 2.83 ppm, (4H, t), 2.7 ppm, (4H, m), 1.41 ppm, (12H, m), 1.00 ppm, (6H, m).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for about 20 hours
  3. additionis added
  4. customhydrolysis
  5. extractionThe aqueous phase is extracted with about 2×100 mL of CH2Cl2
  6. washThe organic phases combined are back washed with about 200 mL water
  7. dry with materialdried over MgSO4
  8. customThe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-10b3bd7241a243e191b9bf634878b177
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875205B2

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