Citric Acid → HCID 57879323, compound

HRID 1673387Notes

Reaction equation

HRID 1673387 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].C(=O)([O-])[O-].[Cs+].[Cs+].[C:15]([NH:23][C:24]1[CH:36]=[C:35]([CH:37]=[CH2:38])[CH:34]=[CH:33][C:25]=1[C:26]([O:28]C(C)(C)C)=[O:27])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(P([Pd+])C2CCCCC2)CCCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:15]([NH:23][C:24]1[CH:36]=[C:35](/[CH:37]=[CH:38]/[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:8])[CH:34]=[CH:33][C:25]=1[C:26]([OH:28])=[O:27])(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

9

Reactant 4

HCID 311Citric AcidHCID 51282-IodotolueneHCID 10796Cesium carbonateHCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

Product 1

HCID 57879323HCID 57879323, compound

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178527697HCID 178527697, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

0.031 mL of 2-iodotoluene, 81 g of cesium carbonate, 12 mg of tetrabutylammonium bromide and 19 mg of polymer supported di(acetato) dicyclohexylphosphino palladium(II) were added to 1.0 mL of toluene solution containing 40 mg of tert-butyl 2-(benzamido)-4-vinylbenzoate at room temperature and stirred at 110° C. for 24 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 the solvent was evaporated under reduced pressure after washed with 10% citric acid aqueous solution, 5 mL of trifluoroacetic acid was added to the obtained residue and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and the obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 65-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 2.8 mg of 2-(benzamido)-4-((E)-2-(2-methylphenyl)vinyl)benzoic acid as while solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. washafter washed with 10% citric acid aqueous solution, 5 mL of trifluoroacetic acid
  5. additionwas added to the obtained residue
  6. stirringstirred at room temperature for 1 hour
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 65-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record
ord-02f7dec6e2f74c98ab660c388c4a68d7
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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