Boron tribromide → 4-Bromo-6-hydroxy-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

A −78° C. suspension of Example 104A (100 mg, 0.41 mmol) in dichloromethane (13 mL) was treated dropwise with 1M BBr3 in dichloromethane (1.2 mL, 1.2 mmol), stirred at −78° C. for 1 hour, and stirred at room temperature for 2 hours. The mixture was treated with additional 1M BBr3 in dichloromethnae (0.8 mL), heated to reflux overnight, then cooled to room temperature, and partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4), filtered, and concentrated to give 91 mg (97%) of the desired product. MS (ESI(−)) m/226, 228 (M−H)−.

Provenance & Evidence