반응 #171150

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2-bromo-3-decanyldithieno[3,2-b:2′,3′-d]thiophene

1-decyne

→

compound

수율 93.0%

3-decanyl-6-dec-1-ynyldithieno[3,2-b:2′,3′-d]thiophene

수율 93.0%

용매

triethylamine

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후처리

1. 1
   기타This mixture is bubbled with nitrogen for 5 minutes
2. 2
   기타Triethylamine is evaporated
3. 3
   workup.ADDITIONhexane (150 mL) is added
4. 4
   여과The 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 eluting with hexane

실험 절차

2-bromo-3-decanyldithieno[3,2-b:2′,3′-d]thiophene (92) (4.16 g, 0.01 mol) is mixed with 1-decyne (3.6 g, 0.026 mol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) and copper(I) iodide (0.19 g, 1.0 mmol) in triethylamine (80 mL). This mixture is bubbled with nitrogen for 5 minutes and then heated to 130° C. under argon for 16 hours. Triethylamine is evaporated and hexane (150 mL) is added. The mixture is filtered to remove solid salts and 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 eluting with hexane to yield the target compound (3.87 g, 93.0% yield). 1HNMR (CD2Cl2): δ 7.36 (d, 1H), 7.30 (d, 1H), 2.82 (t, 2H), 2.49 (t, 2H), 1.63-1.27 (m, 28H), 0.88 (m, 6H).

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