反应详情

A mixture of 3-iodonitrobenzene (2.0 g, 8.0 mmol), bis(triphenylphosphine)palladium(II) chloride (0.30 g, 0.40 mmol) and copper(I) iodide (0.080 g, 0.40 mmol) in 25 mL of Et3N was degassed by freeze/pump/thaw technique (three times). Trimethylsilylacetylene (1.0 g, 10 mmol) was added and the mixture was stirred for 12 hours. The reaction mixture was filtered through a celite pad and the pad was rinsed with CH2Cl2. The filtrate was washed with sat. NH4Cl (aq.) and brine and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (Hexane, then EtOAc;Hexanes =1:30) to afford trimethyl((3-nitrophenyl)ethynyl)silane (1.65 g, 94%): 1H-NMR (300 MHz, CDCl3) δ 8.32 (dd, J=1.8, 1.8 Hz, 1H), 8.17 (ddd, J=8.4, 2.1, 0.9 Hz, 1H), 7.76 (ddd, J=7.5, 1.2, 1.2 Hz, 1H), 7.49 (dd, J=8.1, 8.1 Hz, 1H), 0.28 (s, 9H).

1. customwas degassed by freeze/pump/thaw technique (three times)
2. filtrationThe reaction mixture was filtered through a celite pad
3. washthe pad was rinsed with CH2Cl2
4. washThe filtrate was washed with sat. NH4Cl (aq.) and brine
5. dry with materialthe organic layer was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by column chromatography (Hexane