Toluene → HCID 57667801, compound

HRID 2191616Notes

Reaction equation

HRID 2191616 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[F:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:19][C:17]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([NH:8][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[CH:18]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 96054-FluoroiodobenzeneHCID 10796Cesium carbonateHCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 1

HCID 57667801HCID 57667801, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 634876Binap, (A+-)-Catalyst2×HCID 962WaterSolvent

Procedure

To toluene 12 mL solution of methyl 2-amino-4-bromobenzoate 1.2 g were added 1-fluoro-4-iodobenzene 1.5 mL, cesium carbonate 3.4 g, palladium acetate 12 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, palladium acetate 12 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32 mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B (spherical type), eluent; hexane:ethyl acetate=10:1] to give methyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g of pale yellow solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 12 hours
  3. temperaturewas heated
  4. temperaturerefluxed under nitrogen atmosphere for 12 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. washafter sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-257d54bd930140f78f5aee174c88422b
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…