反应详情

温度

82.5 °C

Into a sealable tube was weighed 2.06 g (8.76 mmol) of 1-bromo-3-methanesulfonyl-benzene, 93 mg of palladium acetate, 122 mg of triphenylphosphine, 79 mg of copper (I) iodide, 10.0 mL of triethylamine, and 2.0 mL of trimethylsilylacetylene. The reaction vessel was sealed and was heated at 80-85° C. for 1 h then was filtered of solids with added ethyl acetate. The filtrate was concentrated in vacuo and was purified by silica gel flash chromatography (Jones Flashmaster, 50 g Silica gel, gradient elution from 100% hexanes to 40% ethyl acetate over 30 minutes). Appropriate fractions were combined and concentrated in vacuo affording (3-methanesulfonyl-phenylethynyl)-trimethylsilane as a faintly yellow oil, yield: 1.60 g (72%). 1H NMR (CDCl3): δ 8.04 (s, 1H), 7.88 (d, J=8 Hz, 1H), 7.71 (d, J=8 Hz, 1H), 3.05 (s, 3H), 0.27 (s, 9H).

1. customInto a sealable tube was weighed
2. customThe reaction vessel was sealed
3. filtrationthen was filtered of solids with added ethyl acetate
4. concentrationThe filtrate was concentrated in vacuo
5. customwas purified by silica gel flash chromatography (Jones Flashmaster, 50 g Silica gel, gradient elution from 100% hexanes to 40% ethyl acetate over 30 minutes)
6. concentrationconcentrated in vacuo