Potassium Carbonate → HCID 18455594, Verbindung

HRID 1966312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966312
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[Br:9][C:10]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:13]([CH:14]=[O:15])=[C:12](F)[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CC(OC)(C)C>C(#N)C>[Br:9][C:10]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([N:4]2[CH2:5][CH:6]([CH3:8])[O:7][CH:2]([CH3:1])[CH2:3]2)[CH:11]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 6415002,6-Dimethylmorpholine, cis-HCID 184555954-Bromo-2-fluoro-5-nitrobenzaldehyde

Produkt 1

HCID 18455594HCID 18455594, VerbindungAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of cis-2,6-dimethylmorpholine (1.06 g, 9.20 mmol) in acetonitrile (40 mL) is added to a flask containing 4-bromo-2-fluoro-5-nitrobenzaldehyde (from Step 1) (2.0 g, 8.06 mmol) and potassium carbonate (3.92 g, 28.4 mmol). The resulting slurry is stirred at room temperature for 63 hours. The mixture is poured into MTBE (100 mL) and is washed with water (100 mL) followed by brine (100 mL). The organics are filtered through silica gel and concentrated to give 1.76 g of bright yellow solid. 1H NMR (DMSO-d6) δ 9.93, 8.44, 7.53, 3.74-3.81, 3.48, 2.78, 1.12.

Aufarbeitung

  1. washis washed with water (100 mL)
  2. filtrationThe organics are filtered through silica gel
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-879672e9785b48c9ad9a43d70672da90
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420646B2

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