Boron tribromide → 5,6-Dihydroxy-2,3-dihydro-1H-inden-1-one
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12]C)[C:8](=[O:14])[CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[C:8](=[O:14])[CH2:7][CH2:6]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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)+.
Workup
- waitat 0° C. for 1 hr
- temperatureThe solution was then cooled back to −78° C. with a dry-ice/iPrOH bath
- customquenched with 50 mL of MeOH
- customThe solution was evaporated on a rotary evaporator to dryness
- dissolutionthe solid was re-dissolved in MeOH
- concentrationconcentrated again for two more times
- customThe red solid, the title compound, was used in subsequent reactions without further purification
Sources & evidence
- ORD record
- ord-37ff8e1e8a574d16b3a705e815a0e2af
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196110B2
Reaction notes
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