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

Temperature

80 °C

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%).

1. extractionthe mixture was extracted with ethyl acetate (three times)
2. washThe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
3. dry with materialdried with anhydrous sodium sulfate
4. customThe residue obtained
5. customby removing the solvent under reduced pressure
6. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=80/20-50/50)

ORD record

ord-5cb7f5cdb39b42099885e479370330d4

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2