反应详情

To a solution of 4-bromo-1-methyl-2-nitrobenzene (10 g) in THF (130 mL) was slowly added vinylmagnesium bromide (1 M in THF, 162 mL) at −40° C. under nitrogen atmosphere. The reaction mixture was stirred for 1.5 h and then quenched with sat'd. aq. NH4Cl (50 mL). The mixture was partitioned between EtOAc (500 mL) and water (150 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 1.54 g (16%) of 4-bromo-7-methyl-1H-indole (306) as brown solid: MS (ESI) m/z=209.9 [M+1]+.

1. customat −40° C.
2. customquenched with sat'd
3. customThe mixture was partitioned between EtOAc (500 mL) and water (150 mL)
4. customThe organic layer was separated
5. washwashed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated in vacuo
9. customThe residue was purified by SiO2 chromatography
10. washeluting with 2.5% EtOAc/petroleum ether