Potassium Carbonate → HCID 57889680, compound

HRID 1016200Notes

Reaction equation

HRID 1016200 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH:11]([CH3:13])[CH3:12])[C:5]([OH:7])=[O:6].[C:14]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43](=[O:46])([O-])[O-:44].[K+].[K+].[C]=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[CH:11]([C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[C:43]([O:44][CH3:14])=[O:46])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 448285203-Iodo-4-(propan-2-yl)benzoic acidHCID 178418416HCID 178418416, compound

Product 1

HCID 57889680HCID 57889680, compoundYield 857.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A parr reactor was charged with 3-iodo-4-isopropylbenzoic acid (60 mg, 0.207 mmol), palladium acetate, MeOH (25 mL), 1,3-bis(diphenylphosphino)propane (4.31 mg, 0.021 mmol), and potassium carbonate (57 mg, 0.414 mmol) and pressurized with 80 psi of carbon monoxide gas. The reaction was heated at 75° C. overnight. The reaction was cooled, concentrated, and partitioned between 15 mL water/15 mL methylene chloride. The aqueous portion was acidified with 1 N HCl and extracted with methylene chloride. The organics were dried over sodium sulfate, filtered, and concentrated to yield a yellowish solid (40 mg).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. custompartitioned between 15 mL water/15 mL methylene chloride
  4. extractionextracted with methylene chloride
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-343825e943bf4c6a9730178934cad5bb
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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