Potassium Carbonate → 2,5-Bis-{5'[6-(tert-butyldimethylsilanyloxy)-hexyl]-[2,2']bithiophenyl-5-yl}-thieno[3,2-b]thiophene

HRID 644112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644112
Br[C:2]1[S:6][C:5]2[CH:7]=[C:8](Br)[S:9][C:4]=2[CH:3]=1.[C:11]([Si:15]([CH3:43])([CH3:42])[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[S:27][C:26]([C:28]2[S:29][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:32]=2)=[CH:25][CH:24]=1)([CH3:14])([CH3:13])[CH3:12].[C:44](=[O:47])([O-])[O-].[K+].[K+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Si:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[S:27][C:26]([C:28]2[S:29][C:30]([C:2]3[S:6][C:5]4[CH:7]=[C:8]([C:30]5[S:29][C:28]([C:26]6[S:27][C:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:44][O:47][Si:15]([C:11]([CH3:12])([CH3:14])[CH3:13])([CH3:43])[CH3:42])=[CH:24][CH:25]=6)=[CH:32][CH:31]=5)[S:9][C:4]=4[CH:3]=3)=[CH:31][CH:32]=2)=[CH:25][CH:24]=1)([C:11]([CH3:14])([CH3:12])[CH3:13])([CH3:43])[CH3:42]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 35974552,5-Dibromothieno(3,2-b)thiopheneHCID 588073092-{5'-[6-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-[2,2']bithiophenyl-5-yl}-4,4,5,5-tetramethyl-[1,3,2}dioxaborolane

Produkt 1

HCID 589916242,5-Bis-{5'[6-(tert-butyldimethylsilanyloxy)-hexyl]-[2,2']bithiophenyl-5-yl}-thieno[3,2-b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.05 g) was added to a solution 2,5-dibromothieno[3,2-b]thiophene (0.10 g, 0.34 mmol) in dry THF (30 ml), with stirring, under nitrogen. After 20 min, 2-{5′-[6-(tert-butyl-dimethyl-silanyloxy)-hexyl]-[2,2′]bithiophenyl-5-yl}-4,4,5,5-tetramethyl-[1,3,2}dioxaborolane (0.51 g, 1.01 mmol) and a solution of potassium carbonate (0.28 g, 2.03 mmol) in water (10 ml) were added. The resultant mixture was heated at reflux for 1.5 h. After cooling, water (100 ml) was added and the precipitate filtered off, washed with water and diethyl ether, to give a yellow solid, which was recrystallised with toluene to offer yellow crystals (0.17 g, 57%).

Aufarbeitung

  1. temperatureat reflux for 1.5 h
  2. temperatureAfter cooling
  3. filtrationthe precipitate filtered off
  4. washwashed with water and diethyl ether
  5. customto give a yellow solid, which
  6. customwas recrystallised with toluene

Quellen und Nachweise

ORD-Eintrag
ord-81151031f8a249ada13286f3cb2c58b2
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700643B2

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