Citric Acid → HCID 67343890, compound

HRID 1673561Notes

Reaction equation

HRID 1673561 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].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:49]([NH:57][C:58]1[CH:70]=[C:69](Br)[CH:68]=[CH:67][C:59]=1[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:49]([NH:57][C:58]1[CH:70]=[C:69]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:68]=[CH:67][C:59]=1[C:60]([O:62][C:63]([CH3:65])([CH3:66])[CH3:64])=[O:61])(=[O:56])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

9

Reactant 5

HCID 311Citric AcidHCID 111373-NitrophenolHCID 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 67343890HCID 67343890, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

31 mg of 3-nitrophenol, 79 mg of tripotassium phosphate, 4.7 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 6.8 mg of tris(dibenzylideneacetone)dipalladium(0) 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 2 hours. After the reaction mixture was cooled to room temperature, 4.7 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 6.8 mg of tris(dibenzylideneacetone)dipalladium(0) were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 1 hour. After the reaction mixture was cooled to 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 a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane; ethyl acetate=10:1) to obtain tert-butyl 2-(benzamido)-4-(3-nitrophenoxy)benzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 2 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux under nitrogen atmosphere for 1 hour
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. custominsoluble were removed by filtration
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter washed with a saturated sodium chloride aqueous solution
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical)

Sources & evidence

ORD record
ord-10ce1cd17acf4c95b0d0faadfb833e37
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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