2,4-Dimethoxy-1-nitrobenzene → 1,5-Dimethoxy-2-iodo-4-nitrobenzene

HRID 649853

Reaktionsgleichung

Reaktionsgleichung von HRID 649853
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[I:14](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[I:14][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[O:9][CH3:10]

Komponenten

5

Edukt 2

HCID 786332,4-Dimethoxy-1-nitrobenzeneHCID 56924451Trimethylbenzylammonium Dichloroiodate2×

Produkt 1

HCID 185429691,5-Dimethoxy-2-iodo-4-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysator2×HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a solution of 2,4-dimethoxy-nitrobenzene (1.0 g) in glacial acetic acid (30 mL) is added benzyltrimethylammonium dichloroiodate (1.90 g) and anhydrous zinc chloride (1.0 g) and the mixture is stirred at room temperature under an atmosphere of argon. Additional benzyltrimethylammonium dichloroiodate (0.4 g) is added after 5 hours and again after 24 hours. Additional zinc chloride (0.5 g) and glacial acetic acid (15 mL) is added after 24 hours. The mixture is permitted to stir at room temperature for 3 days and is then filtered, diluted with 5% aqueous sodium bisulfite, and extracted three times with ethyl acetate. These pooled organic extracts are washed successively with 5% aqueous sodium bisulfite, saturated aqueous sodium chloride, then dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure the residue is triturated with hexanes to provide the desired product as a pale yellow solid.

Aufarbeitung

  1. stirringto stir at room temperature for 3 days
  2. filtrationis then filtered
  3. additiondiluted with 5% aqueous sodium bisulfite
  4. extractionextracted three times with ethyl acetate
  5. washThese pooled organic extracts are washed successively with 5% aqueous sodium bisulfite, saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removal of the solvent under reduced pressure the residue
  8. customis triturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-fce9a95bcfd44d0592940bec06ebeda6
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271236B1

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