Hydrochloric Acid → HCID 67119167, compound

Participants

Reaction Conditions

Reaction Steps

After a 2N aqueous sodium carbonate solution (12 ml) and tetrakis(triphenylphosphine)palladium (0) (504 mg, 0.436 mmol) were added to a solution of methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (2.41 g, 8.73 mmol) obtained in Example (12-1) and 4-bromo-3-chlorophenol (2.17 g, 10.5 mmol) in a mixture of toluene-ethanol (5:1, 36 ml), the mixture was stirred at 110° C. for 8 hours. After the temperature of the reaction mixture was returned to room temperature and ethanol (12 ml) and a 1N aqueous sodium hydroxide solution (15 ml, 15 mmol) were added thereto, the mixture was stirred at 60° 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=85/15-50/50) to give (2′-chloro-4′-hydroxy-1,1′-biphenyl-4-yl)acetic acid as a pale yellow powder (1.95 g, yield: 85%).

Provenance & Evidence