Acetic Acid → 2-((2-Methoxy-4-(trifluoromethyl)phenyl)amino)-5-nitrophenol

HRID 528637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528637
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[O:29][CH3:30].C(O)(=O)C.C(Cl)Cl.CO.[NH4+].[OH-]>CN(C=O)C.[Cu]I.CCOC(C)=O>[CH3:30][O:29][C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:27])[F:28])[CH:23]=[CH:24][C:19]=1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11]

Komponenten

9

Edukt 5

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 49847212-Amino-5-NitrophenolHCID 49911451-Bromo-2-methoxy-4-(trifluoromethyl)benzeneHCID 21896990Dichloromethane methanol ammonium hydroxide

Produkt 1

HCID 897612612-((2-Methoxy-4-(trifluoromethyl)phenyl)amino)-5-nitrophenolAusbeute 24,65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Dissolved 2-amino-5-nitrophenol (4.0 g, 26.0 mmol), cesium carbonate (23.25 g, 71.4 mmol), and copper(i) iodide (4.94 g, 26.0 mmol) in DMF (43.3 ml) in a 250 mL sealed tube and stirred at 25° C. for 30 min. Then added 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (5.52 g, 21.63 mmol) and stirred for 18 h at 100° C. Added acetic acid (8.67 ml, 151 mmol) to neutralize base and product. Diluted the reaction with a solution of DCM/MeOH/NH4OH (90:10:1) and filtered through a frit of silica to remove some of the copper and base, rinsing with more of the solution. The collected eluent was concentrated, then purified using silica gel chromatography using a gradient of (0-100%) Hex:EtOAc to yield 2-((2-methoxy-4-(trifluoromethyl)phenyl)amino)-5-nitrophenol (1.75 g, 5.33 mmol, 24.65% yield) as a yellow solid.

Aufarbeitung

  1. customsealed tube
  2. additionDiluted
  3. filtrationfiltered through a frit of silica
  4. customto remove some of the copper and base
  5. washrinsing with more of the solution
  6. concentrationThe collected eluent was concentrated
  7. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-78c192b07ca347a39500307d3f60f6bc
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346798B2

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