1,3-Dibromopropane → 2-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

HRID 1057988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057988
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[Br:19][CH2:20][CH2:21][CH2:22]Br>CN(C)C=O.ClCCl>[Br:19][CH2:20][CH2:21][CH2:22][O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

6

Edukt 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

Produkt 1

HCID 186726462-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A stirred mixture of 2-methoxy-5-nitrophenol (5.0 g. 29.6 mmol) and powdered potassium carbonate (6.5 g, 47.4 mmol) in dimethylformamide (50 mL) was treated with 1,3-dibromopropane (80.8 g, 0.4 mol), heated to 90° C. for 2 h, cooled, diluted with dichloromethane (250 mL), and filtered. The filtrate was concentrated in vacuo and the residue was crystallized from methanol. The resulting solid was triturated with 30% ethyl acetate/hexane and then with boiling 30% ethyl acetate/hexane. The combined organic phases were concentrated in vacuo to give the title compound: 1H NMR (300 MHz, CDCl3) δ7.92 (dd, 1H), 7.75 (d, 1H), 6.92 (dd, 1H), 4.20 (t, 2H), 3.95 (s, 3H), 3.62 (t, 2H), 2.40 (m, 2H).

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was crystallized from methanol
  5. customThe resulting solid was triturated with 30% ethyl acetate/hexane
  6. concentrationThe combined organic phases were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0c9b52799a784be0bfb5b459fa1cf985
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515027B1

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