Water → Methyl 2-[4-(4-methoxyphenyl)phenyl]acetate

HRID 2076582Notes

Reaction equation

HRID 2076582 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.O>C1(C)C(CCO)=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 316783Methyl 2-(4-bromophenyl)acetate

Product 1

HCID 75488472Methyl 2-[4-(4-methoxyphenyl)phenyl]acetateYield 96.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 882672-Methylphenethyl alcoholSolvent

Procedure

After a 1M aqueous sodium carbonate solution (2.8 ml) and tetrakis(triphenylphosphine)palladium (0) (116 mg, 0.10 mmol) were added to a solution of methyl (4-bromophenyl)acetate (573 mg, 2.50 mmol) obtained in Example (3-1) and 4-methoxyphenylboronic acid (380 mg, 2.50 mmol) in a mixture of toluene-ethanol (6:1, 6 ml), the mixture was heated under reflux for 4 hours. 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 a yellow solid. It was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=95/5-80/20) to give methyl (4′-methoxy-1,1′-biphenyl-4-yl)acetate as a pale yellow powder (617 mg, yield: 96%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customwas returned to room temperature
  4. extractionextracted with ethyl acetate three times
  5. washThe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customto give a yellow solid
  9. customIt was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=95/5-80/20)

Sources & evidence

ORD record
ord-4323efb51140494587701b18a0c93c92
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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