反应详情

To a solution of 4-bromo-1-fluoro-2-nitrobenzene (1.1 g, 5.0 mmol) in THF (20 mL) at −40° C. under nitrogen atmosphere was added slowly vinylmagnesium bromide (1 M in THF, 15.5 mL, 15.5 mmol). The reaction mixture was stirred for 1.5 h then quenched with saturated NH4Cl aqueous solution (10 mL). The mixture was partitioned between EtOAc (300 mL) and water (50 mL). The organic layer was separated, washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by SiO2 chromatography eluting with 2.5% EtOAc/petroleum ether to afford 0.125 g (12%) of 4-bromo-7-fluoro-1H-indole (110) as brown oil: MS (ESI) m/z=214 [M−1]+.

1. customthen quenched with saturated NH4Cl aqueous solution (10 mL)
2. customThe mixture was partitioned between EtOAc (300 mL) and water (50 mL)
3. customThe organic layer was separated
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe residue was purified by SiO2 chromatography
9. washeluting with 2.5% EtOAc/petroleum ether