Sodium Carbonate → Ethyl 3'-methoxy[1,1'-biphenyl]-2-carboxylate

HRID 278165

Reaction equation

HRID 278165 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[Na+].[Na+].[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1>COCCOC.O.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]=[C:25]([C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 80186Ethyl 2-bromobenzoateHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 22627113Ethyl 3'-methoxy[1,1'-biphenyl]-2-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a stirred solution of ethyl 2-bromobenzoate (13.7 g, 59.8 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.46 g, 3.0 mmol) in 1,2-dimethoxyethane (600 mL) was added 2 M aq. Na2CO3 (60 mL, deoxygenated). 3-Methoxyphenylboronic acid (10.0 g, 65.8 mmol) was added in 1,2-dimethoxyethane (80 mL) and the mixture was heated to 100° C. for 36 hours, under argon atmosphere. The mixture was cooled, diluted with water (1 L) and extracted with EtOAc (2×800 mL). The combined organic extracts were washed with sat. aq. NaHCO3, then brine, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with a gradient of 0-10% EtOAc in hexane, to give the titled product as a colorless oil.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (2×800 mL)
  3. washThe combined organic extracts were washed with sat. aq. NaHCO3
  4. dry with materialbrine, then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with a gradient of 0-10% EtOAc in hexane

Sources & evidence

ORD record
ord-14c522aeffb34f50a4034657d167f1c8
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Linked notes

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