6-Methoxy-alpha-tetralone → 6-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

Participants

Reaction Steps

Heat a solution of 6-methoxytetralone (9.6 g, 54 mmol), 4-bromothioanisole (25 mL, 123 mmol), sodium tert-butoxide (20.9 g, 217 mmol), palladium (II) acetate (610 mg, 2.72 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.8 g, 2.72 mmol) and toluene (150 mL) at reflux for 18 hours, then cool to ambient temperature and evaporate to dryness under reduced pressure. Dissolve the residue in dichloromethane and wash with aqueous hydrochloric acid (1N), filter through celite and chromatograph twice on silica gel with hexane/ethyl acetate mixtures to give 2.41 g of 6-methoxy-2-(4-methylsulfanyl-phenyl)-naphthalen-1-ol (15%).

Provenance & Evidence