Potassium Carbonate → Methyl 2-(1,1-dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662349Notes

Reaction equation

HRID 1662349 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1OS(C(F)(F)F)(=O)=O)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+]>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>[CH3:2][C:1]([C:5]1[CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:12]=[CH:13][C:14]=1[C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([O:25][CH2:23][CH3:24])[CH:31]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27739203-Ethoxybenzeneboronic acidHCID 57467613Methyl 3-tert-butyl-4-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 57706553Methyl 2-(1,1-dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A dry round bottom flask containing 8.7 (1.13 g, 3.31 mmol), 3-ethoxyphenylboronic acid (available from Aldrich) (1.10 g, 6.63 mmol), tetrakis(triphenylphosphine)palladium (0.39 g, 0.340 mmol), and potassium carbonate (1.41 g, 10.20 mmol) was evacuated and backfilled three times with argon. Dry DMF (10.000 mL) was then added via syringe under argon. The mixture was then heated at 80° C. and monitored with TLC. After 20 hours, the reaction was cooled to room temperature and diluted with water. The mixture was extracted three times with EtOAc and then concentrated under reduced pressure. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-25% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 41.1 as a colorless oil (0.87, 84%). MS ESI (pos.) m/e: 313.1 (M+H)+.

Workup

  1. customwas evacuated
  2. additionDry DMF (10.000 mL) was then added via syringe under argon
  3. temperaturethe reaction was cooled to room temperature
  4. additiondiluted with water
  5. extractionThe mixture was extracted three times with EtOAc
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-25% EtOAc in hexanes)
  8. additionFractions containing the desired product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-922abcbefc3c4c458d46ef22a6458391
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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