4-bromo-7-fluoro-5-methyl-1H-indole

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-bromo-4-fluoro-2-methyl-5-nitro-benzene (20 g, 0.086 mol) in THF (250 mL) at −78° C. was added vinylmagnesium bromide (300 ml, 0.3 mol) dropwise, then the mixture was stirred at −78° C. for 2 h. Water was added and the reaction allowed to warm slowly to rt. The mixture was extracted with EtOAc, dried over Na2SO4, and concentrated. The crude product was purified by silica gel column chromatography to afford 4-bromo-7-fluoro-5-methylindole (3.2 g, 16.4%). to warm slowly to rt The mixture was extracted with EtOAc dried over Na2SO4 concentrated The crude product was purified by silica gel column chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-bromo-4-fluoro-2-methyl-5-nitro-benzene (20 g, 0.086 mol) in THF (250 mL) at −78° C. was added vinylmagnesium bromide (300 ml, 0.3 mol) dropwise, then the mixture was stirred at −78° C. for 2 h. Water was added and the reaction allowed to warm slowly to rt. The mixture was extracted with EtOAc, dried over Na2SO4, and concentrated. The crude product was purified by silica gel column chromatography to afford 4-bromo-7-fluoro-5-methylindole (3.2 g, 16.4%). to warm slowly to rt The mixture was extracted with EtOAc dried over Na2SO4 concentrated The crude product was purified by silica gel column chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-bromo-4-fluoro-2-methyl-5-nitro-benzene (20 g, 0.086 mol) in THF (250 mL) at −78° C. was added vinylmagnesium bromide (300 ml, 0.3 mol) dropwise, then the mixture was stirred at −78° C. for 2 h. Water was added and the reaction allowed to warm slowly to rt. The mixture was extracted with EtOAc, dried over Na2SO4, and concentrated. The crude product was purified by silica gel column chromatography to afford 4-bromo-7-fluoro-5-methylindole (3.2 g, 16.4%). to warm slowly to rt The mixture was extracted with EtOAc dried over Na2SO4 concentrated The crude product was purified by silica gel column chromatography