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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence