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

HRID 1662330Notes

Reaction equation

HRID 1662330 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].[CH3:23][O:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.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:29]1[CH:28]=[CH:27][CH:26]=[C:25]([O:24][CH3:23])[CH:30]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 57467613Methyl 3-tert-butyl-4-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 57705757Methyl 2-(1,1-dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A dry round bottom flask containing 8.7 (1.40 g, 4.1 mmol), 3-methoxyphenylboronic acid (available from Aldrich) (1.27 g, 8.34 mmol), tetrakis(triphenylphosphine)palladium (0.49 g, 0.42 mmol), and potassium carbonate (1.71 g, 12.36 mmol) was evacuated and backfilled three times with argon. Dry DMF (12.0 mL) was added via syringe under argon, and the mixture was then heated to 100° C. and monitored by TLC. After 2 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%-15% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 12.1 as a colorless oil (1.01, 82%). MS ESI (pos.) m/e: 299.2 (M+H)+.

Workup

  1. customwas evacuated
  2. additionDry DMF (12.0 mL) was 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%-15% EtOAc in hexanes)
  8. additionFractions containing the desired product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-909a0b3af21f4b57b8fab7b77a212fbd
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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