Methanol → 2-Methoxy-2'-nitro-4,4'-dibromobiphenyl

HRID 71906

Reaktionsgleichung

Reaktionsgleichung von HRID 71906
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[N+:15]([O-:17])=[O:16])=[C:4]([N+]([O-])=O)[CH:3]=1.[CH3:21][O-:22].[Na+].CO>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[N+:15]([O-:17])=[O:16])=[C:4]([O:22][CH3:21])[CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 100466484,4'-Dibromo-2,2'-dinitro-1,1'-biphenylHCID 10942334Sodium Methoxide

Produkt 1

HCID 99774712-Methoxy-2'-nitro-4,4'-dibromobiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To the solution of 4,4′-dibromo-2,2′-dinitro-biphenyl (6.58 g, 16.5 mmol) in DMF (50 ml) at 0° C. was added a solution of sodium methoxide in Methanol (4.4 M, 4.5 ml, 19.8 mmol). The mixture was stirred at 25° C. for 12 hours and was poured into ice-water (140 ml). The mixture was extracted with EtOAc (2×). The combined organic phase was washed with water and brine and dried with Na2SO4. Concentration under reduced pressure gave pale solid. The re-crystallization from CH3CN/MeOH gave 4,4′-dibromo-2-methoxy-2′-nitro-biphenyl as a white solid (3.76 g).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (2×)
  2. washThe combined organic phase was washed with water and brine
  3. dry with materialdried with Na2SO4
  4. concentrationConcentration under reduced pressure
  5. customgave pale solid
  6. customThe re-crystallization from CH3CN/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-e89ee20782544542ac34d10b76178c93
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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