Potassium Carbonate → HCID 56833647, Verbindung

HRID 505519

Reaktionsgleichung

Reaktionsgleichung von HRID 505519
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Br:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN1C(=O)CCC1>[Br:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:20][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 185552,3-DichloronitrobenzeneHCID 25517Ammonium ChlorideHCID 226301803-Bromo-5-chlorophenol

Produkt 1

HCID 56833647HCID 56833647, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

2,3-dichloronitrobenzene (764 mg, 3.99 mmol), 3-bromo-5-chlorophenol (1.65 g, 7.98 mmol) and potassium carbonate (661 mg, 4.79 mmol) were suspended in NMP (5 mL) and placed in an oil bath at 120° C. After 2 hours, the reaction was allowed to cool to room temperature, saturated aqueous ammonium chloride (10 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with dilute brine (4×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by automated column chromatography on silica gel (80 g), eluting with 0-100% CH2Cl2/hexanes to yield the title compound. 1H NMR (CD3CN) δ 8.02 (dd, J=8.3 Hz, J=1.5 Hz, 1H), 7.88 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.52 (dd, J=8.2 Hz, J=8.3 Hz, 1H), 7.38 (m, 1H), 7.07 (m, 1H), 6.97 (m, 1H).

Aufarbeitung

  1. customplaced in an oil bath at 120° C
  2. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic fractions were washed with dilute brine (4×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by automated column chromatography on silica gel (80 g)
  8. washeluting with 0-100% CH2Cl2/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-87d3c660e6a54c859f4fba2caddc8efa
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

Verknüpfte Notizen

Wird geladen…