Water → Methyl (2-chloro-4'-methoxy-1,1'-biphenyl-4-yl)acetate

HRID 2076623Notes

Reaction equation

HRID 2076623 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:11]=[CH:12][C:13]=1OS(C(F)(F)F)(=O)=O.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.O>C1(C)C(CCO)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:11]=[CH:12][C:13]=1[C:32]1[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 3564187Methyl 2-[3-chloro-4-(trifluoromethylsulfonyloxy)phenyl]acetate

Product 1

HCID 86088062Methyl (2-chloro-4'-methoxy-1,1'-biphenyl-4-yl)acetateYield 66%

Reagents, catalysts & solvents 3

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 882672-Methylphenethyl alcoholSolvent

Conditions

Temperature
100 °C

Procedure

After a 2M aqueous sodium carbonate solution (1.5 ml), tris(dibenzylideneacetone)dipalladium (0) (23 mg, 25 μmol) and bis(2-diphenylphosphinophenyl)ether (DPEphos) (28 mg, 52 μmol) were added to a solution of methyl (3-chloro-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate (317 mg, 1.0 mmol) obtained in Example (23-1) and 4-methoxyphenylboronic acid (152 mg, 1.0 mmol) in a mixture of toluene-ethanol (5:1, 9 ml), the mixture was stirred at 100° C. for 5 hours under stirring. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water and 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 solvent was removed under reduced pressure to give methyl (2-chloro-4′-methoxy-1,1′-biphenyl-4-yl)acetate as a solid (192 mg, yield: 66%).

Workup

  1. stirringunder stirring
  2. customwas returned to room temperature
  3. extractionextracted 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 solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-15a71fa011714093b6096f2c84e039fb
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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