Hydrochloric Acid → HCID 67119167, compound

Temperature

110 °C

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%).

1. customwas returned to room temperature
2. stirringthe mixture was stirred at 60° C. for 3 hours
3. extractionthe mixture was extracted with ethyl acetate (three times)
4. washThe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
5. dry with materialdried with anhydrous sodium sulfate
6. customThe residue obtained
7. customby removing the solvent under reduced pressure
8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=85/15-50/50)

ORD record

ord-5d3d686420504882b36b61cf6cdde852

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2