Hydrochloric Acid → 1-Chloro-3-methoxy-2-nitrobenzene

HRID 334589

Reaktionsgleichung

Reaktionsgleichung von HRID 334589
N([O-])=O.[Na+].[CH3:5][O:6][C:7]1[C:8]([N+:14]([O-:16])=[O:15])=[C:9](N)[CH:10]=[CH:11][CH:12]=1.C([O-])(O)=O.[Na+].[ClH:22]>O>[Cl:22][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[C:8]=1[N+:14]([O-:16])=[O:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 104647003-Methoxy-2-nitroanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 2322681-Chloro-3-methoxy-2-nitrobenzeneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of sodium nitrite (180 mg, 2.60 mmol) in water (0.5 mL) was added dropwise to a solution of 3-methoxy-2-nitro-phenylamine (400 mg, 2.38 mmol, Example 86(A)) in HCl (37%, 3.9 mL) at 0° C. over one hour period. Then the reaction mixture was added to a cold (0° C.) solution of CuCl2 (640 mg, 4.76 mmol) in HCl (6 N, 3.5 mL). The resulting green solution was stirred at room temperature for 2 days. Then, the reaction mixture was poured onto ice and neutralized carefully with a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic phase was washed with brine, dried over MgSO4, filtered and evaporated to yield 293 mg (1.56 mmol, 66%) of 1-chloro-3-methoxy-2-nitrobenzene as a brown oil.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with AcOEt
  2. washThe resulting organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d931b7c2ec124d23b6d81acaa465563b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883826B2

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