1,2-Dibromoethane → 4-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine

HRID 1041651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041651
[Br:1][CH2:2][CH2:3]Br.[N:5]1([C:11]2[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([OH:17])[CH:16]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].C1(O)C=CC=CC=1.BrC(Br)C>C(#N)C.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][O:17][C:15]1[CH:16]=[C:11]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[CH:12]=[CH:13][C:14]=1[N+:18]([O-:20])=[O:19]

Komponenten

7

Edukt 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27993995-Morpholino-2-nitrophenolHCID 67263526Phenol dibromoethane

Produkt 1

HCID 672636974-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholineAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1,2-Dibromoethane (1.50 mL, 17.4 mmol) was added to 5-Morpholin-4-yl-2-nitro-phenol (0.792 g, 3.53 mmol) and Potassium carbonate (1.71 g, 12.4 mmol) in Acetonitrile (40 mL) and the reaction was stirred under an atmosphere of Nitrogen at room temperature for 72 h (no change by HPLC), then was brought to reflux. After 4d, 1H-NMR indicated that the assumed starting material my LCMS was in actuality the 2:1 phenol-dibromoethane adduct. The reaction was cooled, diluted with ethyl acetate and filtered, conc. onto 5 g Celite. Chromatography (ISCO, 40 g, 0-40% EtOAc:Hex) afforded 4-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine (447 mg, 38%) as a colorless oil. 1H-NMR (CDCl3): 7.99 (d, 1H, J=8.8 Hz), 6.48 (m, 1H), 6.36 (d, 1H, J=1.5 Hz), 4.39 (t, 2H, J=6.8 Hz), 3.85 (t, 4H, J=4.8 Hz), 3.71 (t, 2H, J=6.8 Hz), 3.34 (t, 4H, J=4.8 Hz).

Aufarbeitung

  1. temperatureto reflux
  2. temperatureThe reaction was cooled
  3. filtrationfiltered, conc. onto 5 g Celite

Quellen und Nachweise

ORD-Eintrag
ord-101c9f3936644fd5b1491b78a4048b73
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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