Ammonium Chloride → 7-bromo-4-fluoro-1H-indole

Participants

Reaction Steps

Vinylmagnesium bromide (1 M in THF, 681.5 mL) was added to a solution of 1-bromo-4-fluoro-2-nitrobenzene (D39) (52.0 g) in anhydrous THF (500 mL) dropwise at −78° C. The mixture was allowed to warm to room temperature and stirred for 2 hours. TLC indicated the reaction was complete. The reaction mixture was poured into saturated aqueous NH4Cl solution. The mixture was extracted with EtOAc (3×200 mL). The organic solution was dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography on silica gel to afford 7-bromo-4-fluoro-1H-indole (D40) (20.0 g) as a white solid.

Provenance & Evidence