Boron tribromide → HCID 21966485, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyl-6-methoxy-3,3,5-trimethyl-1,3-dihydro-indol-2-one (1.52 g, 5.15 mmol) in anhydrous dichloromethane (50 mL) was added slowly, under argon at −78° C., BBr3 (0.87 mL, 9.27 mmol). The reaction was warmed up to −20° C. and stirred overnight at room temperature. Water and the layer separated. The aqueous layer was neutralized with NaHCO3 and extracted with dichloromethane. The organic combined extract was washed with aqueous NaHCO3, water and brine, dried over MgSO4, filtered and evaporated to give 1-benzyl-6-hydroxy-3,3,5-trimethyl-1,3-dihydro-indol-2-one (93% yield). 1H NMR (300 MHz; CDCl3): 1.38 (s, 6 H), 2.19 (s, 3 H), 4.82 (s, 2 H), 5.47 (br s, 1 H), 6.26 (s, 1 H), 6.93 (s, 1 H), 7.26 (m, 5 H).

Provenance & Evidence