6-Bromo-8-(2-ethylhexoxy)-4-(2-ethylhexyl)thieno[2,3-f]benzothiophene → 4-(2-Ethylhexoxy)-8-(2-ethylhexyl)thieno[2,3-f]benzothiophene-2-carbonitrile
Reaktionsgleichung
Br[C:2]1[S:3][C:4]2[C:10]([CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])=[C:9]3[CH:19]=[CH:20][S:21][C:8]3=[C:7]([O:22][CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])[C:5]=2[CH:6]=1.[Cu][C:32]#[N:33]>>[CH2:29]([CH:24]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][O:22][C:7]1[C:8]2[S:21][CH:20]=[CH:19][C:9]=2[C:10]([CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])=[C:4]2[S:3][C:2]([C:32]#[N:33])=[CH:6][C:5]=12)[CH3:30]Komponenten
3
Versuchsvorschrift
A dry 100-mL three-neck flask, equipped with a condenser, charged with 6-bromo-8-(2-ethylhexoxy)-4-(2-ethylhexyl)thieno[2,3-f]benzothiophene (4.2 g, 8.2 mmol) and flushed with N2. Deoxygenated pyridine (15 mL, 0.5 M) was then added via syringe. Copper (I) cyanide (2.2 g, 25 mmol) was added to the reaction flask and the mixture was evacuated and refilled with nitrogen three times. The reaction flask was heated to reflux for 48 hours. As the reaction was completed, the reaction mixture was poured into 50 mL of water and extracted with MTBE (50 mL) three times. The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgSO4). After the product was filtered, the solvent was removed by rotary evaporation. The product was purified using column chromatography on silica gel with hexanes/ethyl acetate (gradient) to yield oil (1.4 g, 38%).