Potassium Carbonate → HCID 22491026, compound

HRID 2180457Notes

Reaction equation

HRID 2180457 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7]([CH3:15])([CH3:14])[CH:6]=[C:5]2OS(C(F)(F)F)(=O)=O.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>C1(C)C=CC=CC=1.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>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7]([CH3:15])([CH3:14])[CH:6]=[C:5]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 20779605HCID 20779605, compound2×

Product 1

HCID 22491026HCID 22491026, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of trifluoro-methanesulfonic acid 6-bromo-7-methoxy-2,2-dimethyl-2H-chromen-4-yl ester (Compound 7, 2.14 g, 5.30 mmol) in 35 mL of anhydrous toluene was first degassed by bubbling with argon for 15 min. Phenylboronic acid (650 mg, 5.30 mmol), potassium carbonate (1.47 g, 10.6 mmol), lithium chloride (632 mg, 14.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (270 mg, 0.53 mmol) were added. After stirring at 90° C. for 12 h, the mixture was cooled to room temperature and quenched with water. The product was extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo and purified by column chromatography (silica gel, 5% ethyl acetate in hexane) to give the title compound as a foam.

Workup

  1. customby bubbling with argon for 15 min
  2. temperaturethe mixture was cooled to room temperature
  3. customquenched with water
  4. extractionThe product was extracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe filtered solvent was concentrated in vacuo
  8. custompurified by column chromatography (silica gel, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d3db9d24817a4ca9860da0683e05bdbb
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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