Potassium Carbonate → HCID 59518165, compound

HRID 1160868Notes

Reaction equation

HRID 1160868 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[CH:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:10]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])=[CH:15][CH:14]=1)([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 728574-Bromo-m-cresolHCID 27734804-Isopropylphenylboronic acid

Product 1

HCID 59518165HCID 59518165, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

4-Bromo-3-methylphenol (1.87 g, 10 mmol), 4-isopropyl phenyl boronic acid (2.0 g, 12 mmol), potassium carbonate (4.1 g, 30 mmol) and palladium acetate (0.112 g, 0.5 mmol) are placed in water (100 mL). And the resulting mixture is stirred at room temperature over night under open air. The mixture is filtered through Celite and extracted with ethyl acetate (3×200 ml). The combined organic layers are washed with water, 1N HCl, water, brine, dried (MgSO4), concentrated and chromatographed to yield the title compound as a white solid (1.9 g).

Workup

  1. filtrationThe mixture is filtered through Celite
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe combined organic layers are washed with water, 1N HCl, water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-0716d4eda2194bb2a03105616059af39
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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