Citric Acid → HCID 67343534, compound

HRID 1673550Notes

Reaction equation

HRID 1673550 reaction equation
[C:1]([NH:9][C:10]1[CH:22]=[C:21](Br)[CH:20]=[CH:19][C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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(OCC)(=O)C.C1(C)C=CC=CC=1>[C:1]([NH:9][C:10]1[CH:22]=[C:21]([O:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH3:24])[CH:27]=2)[CH:20]=[CH:19][C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 311Citric AcidHCID 90073-MethoxyphenolHCID 62657Potassium Phosphate, TribasicHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67343534HCID 67343534, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.0 mg of palladium acetate was added to 5 mL of toluene suspension containing 0.50 g tert-butyl 2-(benzamido)-4-bromobenzoate, 0.18 mL of 3-methoxyphenol, 17 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 0.57 g of tripotassium phosphate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 5 hours. After the reaction mixture was cooled no room temperature, ethyl acetate and 10% citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, 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=6:1]to obtain 0.32 g of tert-butyl 2-(benzamido)-4-(3-methoxyphenoxy)benzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 5 hours
  3. custominsoluble were removed by filtration
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with 10% citric acid aqueous solution
  7. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008

Sources & evidence

ORD record
ord-f7acc523f5324a9dba9279c7d33b63a0
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

Loading…