반응 #171152

반응 방정식

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

1-decyne

triethylamine

→

compound

수율 90.2%

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

수율 90.2%

반응 조건

후처리

1. 1
   기타This mixture is bubbled with nitrogen for 5 minutes
2. 2
   기타The triethylamine is evaporated
3. 3
   workup.ADDITIONhexane (150 mL) is added
4. 4
   여과This mixture is filtered
5. 5
   기타to remove solid salts
6. 6
   세척The organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL)
7. 7
   건조dried over MgSO4
8. 8
   기타The solvent is removed in vacuo
9. 9
   기타the residue is purified by chromatography on silica gel
10. 10
    세척eluted with hexane

실험 절차

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).

출처