Dichloromethane → 2-[4-(3,4-Dichlorophenyl)phenylamino]benzoic acid

HRID 488521Notes

Reaction equation

HRID 488521 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[Cl:8].I[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=[O:23])=[CH:15][CH:14]=1.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].O>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

10

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343303,4-Dichlorobenzeneboronic acidHCID 125070482-[(4-Iodophenyl)amino]benzoic acid

Product 1

HCID 222698272-[4-(3,4-Dichlorophenyl)phenylamino]benzoic acidYield 76%

Reagents, catalysts & solvents 5

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3,4-dichlorophenylboronic acid (880 mg, 2.3 mmol), 2-[(4-iodophenyl)amino]benzoic acid (339 mg, 1 mmol), PdCl2.dppf.CH2Cl2 [1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride, complexed with dichloromethane (1:1)] (67 mg, 0.082 mmol), K2CO3 (829 mg, 6 mmol), and H2O (2 mL) in dioxane (15 mL) was heated to reflux for 1 hour. The reaction mixture was diluted with EtOAc and filtered. The filtrate was treated with 1N HCl, washed with H2O, brine, dried (Na2SO4), and concentrated in vacuum to give a yellow solid. Purification by flash chromatography (silica gel, 10% MeOH/CH2Cl2) yielded 272 mg (0.76 mmol, 76%) of the desired product. mp>220° C.

Workup

  1. temperatureto reflux for 1 hour
  2. filtrationfiltered
  3. additionThe filtrate was treated with 1N HCl
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuum
  7. customto give a yellow solid
  8. customPurification by flash chromatography (silica gel, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f3ba84a3ae5e4967924e799468773db0
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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