Boron Trichloride → Methyl (2-chloro-4'-hydroxy-1,1'-biphenyl-4-yl)acetate

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Reaction Steps

After boron trichloride (1.0N methylene chloride solution, 1.8 ml, 1.8 mmol) was added to a solution of methyl (2-chloro-4′-methoxy-1,1′-biphenyl-4-yl)acetate (228 mg, 0.73 mmol) obtained in Example (23-2) and tetra-n-butylammonium iodide (325 mg, 0.88 mmol) in methylene chloride (4 ml) at −78° C., the temperature of the mixture was raised to room temperature and the mixture was stirred for 2 hours. Ice was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water 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=10/1-2/1) to give methyl (2-chloro-4′-hydroxy-1,1′-biphenyl-4-yl)acetate as a colorless solid (144 mg, yield: 71%).

Provenance & Evidence