Boron tribromide → 5-Hydroxy-1-indanone

HRID 1948657Notes

Reaction equation

HRID 1948657 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 787875-Methoxyindan-1-one

Product 1

HCID 2331475-Hydroxy-1-indanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-methoxyindan-1-one (200 g, 1.235 mol) in 2 L of anhydrous dichloromethane was added BBr3 (234 mL, 2.469 mol) slowly at −78° C. The mixture was warmed slowly to rt and stirred overnight. Then the mixture was poured slowly into ice-water (2 L) with vigorously stirring for 30 min. The result mixture was filtered to give a solid. The filtrate was separated, and the aqueous phase was extracted with EtOAc (2×500 mL). The combined organic phases were washed with brine (1 L) and dried over Na2SO4 and concentrated to dryness to obtain another batch of solid. The combined solids were dried in vacuo to give the title compound. 1H-NMR (400 MHz, MeOD): δ 7.55 (d, J=8.1 Hz, 1H), 6.78-6.84 (m, 2H), 3.03-3.06 (m, 2H), 2.60-2.63 (m, 2H) ppm.

Workup

  1. stirringwith vigorously stirring for 30 min
  2. filtrationThe result mixture was filtered
  3. customto give a solid
  4. customThe filtrate was separated
  5. extractionthe aqueous phase was extracted with EtOAc (2×500 mL)
  6. washThe combined organic phases were washed with brine (1 L)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customto obtain another batch of solid
  10. customThe combined solids were dried in vacuo

Sources & evidence

ORD record
ord-19cf3a48a7ce48d1bf1eb91e515c33a1
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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