Boron tribromide → HCID 135574102, compound

Participants

Reaction Steps

To a solution of 5-(4-methoxyphenyl)quinoline (compound 28) (1.08 g) in methylene chloride (10 ml), a solution of boron tribromide in methylene chloride (1.0 M) (5.5 ml) was added at -40° C. under the inert atmosphere. The reaction mixture was stirred at room temperature for 15 hrs, then it was poured into a cooled solution of sodium hydrocarbonate (NaHCO3). The solution was extracted with ethyl acetate and then the organic layer was washed with satd. NH4Cl aq, water and brine. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The concentrate was crystallized with ethyl ether-methanol (10:1). The resulting precipitate was collected by filtration. 4-(quinoline-5-yl)phenol (29) was obtained as a yellow crystal (0.82 g).

Provenance & Evidence