Boron tribromide → 5,6-Dihydroxy-2,3-dihydro-1H-inden-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 5,6-dimethoxyindan-1-one (Compound 3a) (19 g, 0.094 mole) in 200 mL of methylene chloride was cooled at −78° C. with a dry-ice/iPrOH bath. To this solution was then added 200 mL (0.2 mole) of a 1M solution of BBr3 in CH2Cl2 dropwise. The resulting solution was stirred at −78° C. for 1 hr and then at 0° C. for 1 hr. The solution was then cooled back to −78° C. with a dry-ice/iPrOH bath and quenched with 50 mL of MeOH. The solution was evaporated on a rotary evaporator to dryness, the solid was re-dissolved in MeOH and concentrated again for two more times. The red solid, the title compound, was used in subsequent reactions without further purification. MS m/z 165 (M+H)+.

Provenance & Evidence