Potassium Carbonate → HCID 86628373, compound

HRID 553287Notes

Reaction equation

HRID 553287 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)=[O:14].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:13]=[O:14])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2921892-Formylphenylboronic acidHCID 316783Methyl 2-(4-bromophenyl)acetate

Product 1

HCID 86628373HCID 86628373, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Methyl (4-bromophenyl)acetate (5.9 g), (2-formylphenyl)boronic acid (5.0 g) and potassium carbonate (10.8 g) were combined in a mixture of toluene and methanol [9:1] (50 mL). The resulting mixture was degassed by bubbling nitrogen though for 1 hour. Tetrakis(triphenylphosphine)palladium(0) (1.5 g) was added and the reaction heated to reflux for 12 hours, under nitrogen. The reaction mixture was filtered through a pad of Celite, the filter pad was washed with ethyl acetate and the combined filtrates evaporated. Purification on silica, eluting with a gradient 0 to 10% ethyl acetate in iso-hexane.

Workup

  1. customThe resulting mixture was degassed
  2. customby bubbling nitrogen though for 1 hour
  3. additionTetrakis(triphenylphosphine)palladium(0) (1.5 g) was added
  4. temperaturethe reaction heated
  5. temperatureto reflux for 12 hours, under nitrogen
  6. filtrationThe reaction mixture was filtered through a pad of Celite
  7. washthe filter pad was washed with ethyl acetate
  8. customthe combined filtrates evaporated
  9. customPurification on silica
  10. washeluting with a gradient 0 to 10% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-4dc1049802c549c39040ed589077c819
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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