Hydrochloric Acid → Methyl (2'-fluoro-4'-hydroxy-1,1'-biphenyl-4-yl)acetate

Participants

Reaction Conditions

Reaction Steps

After palladium acetate (II) (50 mg, 0.22 mmol), tri-o-tolylphosphine (135 mg, 0.44 mmol) and a 2N aqueous sodium carbonate solution (15 ml) were added to a solution of methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (2.04 g, 7.39 mmol) obtained in Example (12-1) and 4-bromo-3-fluorophenol (1.69 g, 8.87 mol) in N,N-dimethylformamide (50 ml), the mixture was stirred at 80° C. for 3 hours. The reaction mixture was poured into 0.5N hydrochloric acid and the mixture was extracted with ethyl acetate (three times). The organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=80/20-50/50) to give methyl (2′-fluoro-4′-hydroxy-1,1′-biphenyl-4-yl)acetate (1.13 g, yield: 59%).

Provenance & Evidence