Boron tribromide → HCID 17898073, compound

Participants

Reaction Conditions

Reaction Steps

To (2,6-dimethyl-4-methoxyphenyl)-(3-isopropyl-4-methoxyphenyl) methanone (10) (1 g, 3.20 mmol) in 60 ml of methylene chloride at -78° C. was added 32 mL of boron tribromide (1.0M in methylene chloride). The reaction mixture was stirred at -78° C. for 30 minutes, and then for 12 hours at room temperature. The reaction mixture was washed with water (2×125 mL), dried (MgSO4), and evaporated to give crude product (900 mg). Purification using flash column chromatography (silica gel, 90:10 hexane/ethylacetate) gave 3,5-dimethyl-4-(4'-methoxy-3'-isopropylbenzoyl) phenol (13) (300 mg, 31%) and 3,5-dimethyl-4-(4'-hydroxy-3'-isopropylbenzyl) phenol (14) (450 mg, 49%).

Provenance & Evidence