1-Bromo-2-nitrobenzene → 7-Bromoindole

Participants

Reaction Steps

100 ml (100 mmol) of a tetrahydrofuran solution containing 1.0 M vinylmagnesium bromide was added to a tetrahydrofuran solution (250 ml) containing 5.05 g (25 mmol) of 2-bromonitrobenzene at −40° C. in nitrogen atmosphere, followed by stirring as it was for 40 minutes. The reaction mixture was poured into 500 ml of an aqueous saturated ammonium chloride, and the mixture was extracted with ethyl ether. The extract was dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 2.89 g of the title compound.

Provenance & Evidence