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

HRID 1714443Notes

Reaction equation

HRID 1714443 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]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 750185,6-Dimethoxy-1-indanone2×

Product 1

HCID 115934875,6-Dihydroxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Asolution 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 1 M 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

  1. waitat 0° C. for 1 hr
  2. temperatureThe solution was then cooled back to −78° C. with a dry-ice/iPrOH bath
  3. customquenched with 50 mL of MeOH
  4. customThe solution was evaporated on a rotary evaporator to dryness
  5. dissolutionthe solid was re-dissolved in MeOH
  6. concentrationconcentrated again for two more times
  7. customThe red solid, the title compound, was used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-d8012fef781047429efff38fe1e2f5a0
Source dataset
uspto-grants-2010_09
Patent number
US07795440B2

Reaction notes

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