Sodium Carbonate → HCID 86088095, compound

HRID 2076642Notes

Reaction equation

HRID 2076642 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Na+].[Na+].I[C:30]1[C:31]([CH3:41])=[C:32]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH:33]=[CH:34][CH:35]=1.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1>CN(C)C=O.C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:31]=2[CH3:41])=[CH:46][CH:45]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 201262(4-Methoxyphenyl)boronic acidHCID 70987382HCID 70987382, compound

Product 1

HCID 86088095HCID 86088095, compoundYield 7%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

After palladium acetate (II) (37 mg, 0.16 mmol), tri-o-tolylphosphine (100 mg, 0.327 mmol) and a 2N aqueous sodium carbonate solution (2.5 ml) were added to a solution of methyl (3-iodo-2-methylphenyl)acetate (950 mg, 3.27 mmol) obtained in Example (33-1) and 4-methoxyphenylboronic acid (498 mg, 3.27 mmol) in N,N-dimethylformamide (8 ml), the mixture was stirred at 80° C. for 5 hours. After the reaction mixture was diluted with ethyl acetate and water, the insolubles were removed by filtration through Celite. After the obtained filtrate 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=9/1) to give methyl (4′-methoxy-2-methyl-1,1′-biphenyl-3-yl)acetate as a yellow powder (59 mg, yield: 7%).

Workup

  1. customthe insolubles were removed by filtration through Celite
  2. extractionAfter the obtained filtrate was extracted with ethyl acetate
  3. washthe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-4f69d398f0c3484c9563bcae3d399bd0
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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