Boron tribromide → 5-Hydroxy-4-methyl-2,3-dihydro-1H-inden-1-one

HRID 422205Notes

Reaction equation

HRID 422205 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:8]([CH3:17])=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2>C(Cl)Cl>[OH:6][C:7]1[C:8]([CH3:17])=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57799680HCID 57799680, compound

Product 1

HCID 666729025-Hydroxy-4-methyl-2,3-dihydro-1H-inden-1-oneYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Add dropwise a solution of BBr3 (14.8 g, 59.1 mmol) dissolved in DCM (50 ml) to a solution of 5-Methoxy-4-methyl-1-indanone (Tetrahedron (1970), 26(11), 2599-608) (4.17 g, 23.6 mmol) dissolved in DCM (50 ml) and cooled to −78° C. under nitrogen. After stirring at −78° C. for one hour, remove the cold bath and stir at ambient temperature overnight. Cool the reaction mixture to −78° C. and quench with saturated aqueous NaHCO3. Dilute mixture with water and extract with EtOAc (2×). Wash extracts with water and brine, dry (MgSO4) and concentrate on rotary evaporator to give 5-hydroxy-4-methyl-1-indanone (2.60 g) as an amber solid.

Workup

  1. customremove the cold bath
  2. stirringstir at ambient temperature overnight
  3. temperatureCool the reaction mixture to −78° C.
  4. customquench with saturated aqueous NaHCO3
  5. additionDilute mixture with water
  6. extractionextract with EtOAc (2×)
  7. washWash
  8. dry with materialdry (MgSO4)
  9. concentrationconcentrate on rotary evaporator

Sources & evidence

ORD record
ord-faa8656f6ac344d2be323db4132b49e2
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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