Reaktion #171152

Reaktionsgleichung

2-Bromo-3-decanyldithieno[2,3-d:2′,3′-d′]thieno[3,2-b:4,5-b′]dithiophene

1-decyne

triethylamine

→

compound

Ausbeute 90.2%

2-dec-1-ynyl-3-decanyldithieno[2,3-d:2′,3′-d′]thieno[3,2-b:4,5-b′]dithiophene

Ausbeute 90.2%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis mixture is bubbled with nitrogen for 5 minutes
2. 2
   SonstigeThe triethylamine is evaporated
3. 3
   workup.ADDITIONhexane (150 mL) is added
4. 4
   FiltrationThis mixture is filtered
5. 5
   Sonstigeto remove solid salts
6. 6
   WaschenThe organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL)
7. 7
   Trocknendried over MgSO4
8. 8
   SonstigeThe solvent is removed in vacuo
9. 9
   Sonstigethe residue is purified by chromatography on silica gel
10. 10
    Wascheneluted with hexane

Vorschrift

2-Bromo-3-decanyldithieno[2,3-d:2′,3′-d′]thieno[3,2-b:4,5-b′]dithiophene (2.16 g, 4.6 mmol) (106) is mixed with 1-decyne (1.27 g, 9.2 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 g, 0.46 mmol) in triethylamine (50 mL). This mixture is bubbled with nitrogen for 5 minutes and then heated to 130° C. under argon for 16 hours. The triethylamine is evaporated and hexane (150 mL) is added. This mixture is filtered to remove solid salts. The organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent is removed in vacuo, and the residue is purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3 g, 90.2% yield). 1HNMR (CD2Cl2): δ 7.41 (d, 1H), 7.33 (d, 1H), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m, 6H).

Quelle