反应详情

温度

72 °C

A mixture of 0.2 gm (0.89 mmol) of 1-bromo-3-(4-fluorobut-1-ynyl)benzene, 2 mL of MeOH, 1 mg of methyl(triphenylphosphine)gold (I), 25 μL of conc. H2SO4 and 0.44 mL of H2O was placed in a sealed tube, flushed with argon, heated to 72° C. for 2 h and was cooled. The reaction mixture was diluted with EtOAc, washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the concentrate on silica gel with a gradient of 0% to 20% EtOAc-hexanes gave 1-(3-bromophenyl)-4-fluorobutan-1-one as an oil, 0.086 gm (40% yield); 1H NMR (400 MHz, CDCl3) δ: 2.13 (m, 2H), 3.09 (t, 2H, J=7.1 Hz), 4.53 (dt, 2H, J=5.8, 47.1 Hz), 7.33 (t, 1H, J=7.8 Hz), 7.66 (dq, 1H, J=1.0, 7.8 Hz), 7.55 (dq, 1H, J=1.0, 7.8 Hz), 8.07 (t, 1H, J=1.7 Hz).

1. customwas placed in a sealed tube
2. customflushed with argon
3. temperaturewas cooled
4. additionThe reaction mixture was diluted with EtOAc
5. washwashed sequentially with water and brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. concentrationChromatography of the concentrate on silica gel with a gradient of 0% to 20% EtOAc-hexanes