反应详情

温度

-40 °C

To a solution of 1-bromo-2-fluoro-3-nitrobenzene (2.5 g, 11.3 mmol) in THF (25 mL) at −50° C. was added vinyl magnesium bromide (34 mL, 34 mmol) and the mixture was stirred at −40° C. for 1 h. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield a gum, which was purified by column chromatography over silica gel eluting with EtOAc/hexane to afford pure 6-bromo-7-fluoro-1H-indole. 1H NMR (400 MHz, CDCl3) δ=6.53-6.62 (m, 1H), 7.16-7.25 (m, 2H), 7.29 (d, J=8.34 Hz, 1H) and 8.36 (br. s., 1H); MS (ES+): m/z 214.08 [MH+].

1. customThe reaction was quenched with saturated ammonium chloride solution
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. customevaporated under reduced pressure
6. customto yield a gum, which
7. customwas purified by column chromatography over silica gel eluting with EtOAc/hexane