Bromine → HCID 86723945, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole (1.6 g, 9.6 mmol) in 98% H2SO4 (20 mL), Ag2SO4 (1.6 g, 5.1 mmol) was added and the suspension was stirred under nitrogen for 30 minutes. The mixture was then cooled to −5° C., Br2 (508 μL, 9.9 mmol) was slowly added over 15 minutes and stirring maintained at the same temperature for 1 h. The reaction mixture was slowly poured over 200 mL of water/ice and subsequently filtered through Celite. 50% aqueous NaOH was added to the resulting solution (to pH ═9-10) and the product was extracted with EtOAc (3×). The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (1.58 g) as a dark oil. 1H NMR (DMSO-d6): 7.03 (1H, d), 6.64 (1H, d), 5.59 (1H, s), 3.20 (2H, s), 1.25-1.15 (6H, m). MS: [M+H]+=244.

Provenance & Evidence