Sodium Carbonate → Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylate

HRID 2375152Notes

Reaction equation

HRID 2375152 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)[CH3:2].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)=[O:12])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 22043Ethyl 4-bromobenzoateHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 2764348Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylateYield 95.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromobenzoic acid ethyl ester (2.7 mL, 16.5 mmol), 4-methoxy phenylboronic acid (2.5 g, 16.5 mmol) and sodium carbonate (7.7 g, 72.6 mmol) in toluene:ethanol:water (75 mL:37 mL:37 mL) was flushed with nitrogen for 1 hour. After addition of the tetrakis(triphenylphosphine) palladium (0) catalyst (0.95 g, 0.82 mmol), the reaction was heated at 100° C. overnight. After cooling, the mixture was filtered through Celite which was then washed with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a brown solid. Purification of the residue by flash chromatography with a solvent gradient from 25% to 50% of dichloromethane in hexane provided the title compound (4.05 g, 95.8%) as a pale yellow solid, m.p. 101-103° C.

Workup

  1. customethanol:water (75 mL:37 mL:37 mL) was flushed with nitrogen for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through Celite which
  4. washwas then washed with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a brown solid
  10. customPurification of the residue by flash chromatography with a solvent gradient from 25% to 50% of dichloromethane in hexane

Sources & evidence

ORD record
ord-ede093203e37445cbd44c6aabba36210
Source dataset
uspto-grants-2008_12
Patent number
US07465722B2

Reaction notes

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