Boron tribromide → HCID 19761451, compound

Participants

Reaction Steps

A solution of 5.25 g 2-(2-aminophenyl)-5-methoxy-2,3-dihydro-1H-indole in 115 ml CH2Cl2 was added dropwise to 90.4 ml 1.0M BBr3 in CH2Cl2 at 0° C. The solution was stirred at 0°-5° C. for one hour, and then quenched by dropwise addition of 135 ml water. A total of 400 ml 7.5% NaHCO3 was added dropwise, and the resulting solution was stirred 30 minutes. It was then basified to a pH of ~9 with K2CO3 and extracted with EtOAc. The extracts were washed with saturated NaCl solution, dried (MgSO4), and concentrated to yield 5.10 g solid. Trituration with 5% EtOAc/CH2Cl2 and recrystallization from MeOH/water yielded 1.00 g solid, m.p. 169°-171° C.

Provenance & Evidence