4-Bromo-2-nitroanisole → 4-Bromo-7-methoxy-1H-indole

Participants

Reaction Steps

To a −60° C. solution of 4-bromo-2-nitroanisole (7.89 g, 33.3 mmol) in THF (300 was added vinylmagnesium bromide (1 M in THF, 100 ml, 0.1 mol) while maintaining the reaction temperature below −40° C. The resulting mixture was stirred allowing the temperature to rise to −40° C. in 2 hours. The reaction mixture was then quenched with a saturated solution of NH4Cl (700 ml) and extracted with Et2O (200 ml). The combined organic layers were washed with brine, dried over MgSO4, filtered, concentrated, and purified through flash chromatography affording 4-bromo-7-methoxyindole LII (594 mg, 8% yield).

Provenance & Evidence