Citric Acid → HCID 67341701, compound

HRID 1673557Notes

Reaction equation

HRID 1673557 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[C:47]([NH:55][C:56]1[CH:68]=[C:67](Br)[CH:66]=[CH:65][C:57]=1[C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:47]([NH:55][C:56]1[CH:68]=[C:67]([O:7][C:6]2[CH:1]=[CH:2][C:3]([CH3:8])=[CH:4][CH:5]=2)[CH:66]=[CH:65][C:57]=1[C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

9

Reactant 5

HCID 311Citric AcidHCID 2879P-CresolHCID 62657Potassium Phosphate, TribasicHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane2×HCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67341701HCID 67341701, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.023 mL of p-cresol, 79 mg of tripotassium phosphate, 2.4 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 0.8 mg of palladium acetate were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 1 hour. After the reaction mixture was cooled to room temperature, 4.7 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 1.7 mg of palladium acetate were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1]to obtain tert-butyl 2-(benzamido)-4-(4-methylphenoxy)benzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 1 hour
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux under nitrogen atmosphere for 6 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. washafter washed with a saturated sodium chloride aqueous solution
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008

Sources & evidence

ORD record
ord-7a2ab48b414d4c9c85a65854fa07cb9a
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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