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

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.

1. extractionThe mixture was extracted with EtOAc (3×200 mL)
2. dry with materialThe organic solution was dried over anhydrous sodium sulfate
3. concentrationThe dried solution was concentrated
4. customThe residue was purified by column chromatography on silica gel

ORD record

ord-b0fd5b727f36444db8e5c9eb9873d712

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217028B2