Salicylaldehyde → 2-(4-Fluoro-2-nitrophenoxy)benzaldehyde

HRID 1464438

Reaktionsgleichung

Reaktionsgleichung von HRID 1464438
[H-].[Na+].[CH:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].F[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>CN(C)C=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]=[O:11])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1

Komponenten

5

Edukt 3

HCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 677672,5-Difluoronitrobenzene

Produkt 1

HCID 224840602-(4-Fluoro-2-nitrophenoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium hydride (1.66 g) was added in portions to a stirred solution of salicylaldehyde (8.06 g) in N,N-dimethylformamide (100 mL) under nitrogen. To the resulting yellow solution was added 2,5-difluoro-1-nitrobenzene (10.0 g) and N,N-dimethylformamide (10 mL). The reaction was heated at 50° C. for 18 hours and evaporated under vacuum. The oily mixture was taken up in chloroform, and washed with 1 M NaOH, water, 1 M HCl, and brine, dried over magnesium sulfate, and evaporated under vacuum to an orange oil. The oil was treated with ethyl ether, cooled in an ice bath, and the precipitated product was collected by filtration to yield the title compound as white crystals. Mp: 94°-95° C.

Aufarbeitung

  1. customevaporated under vacuum
  2. washwashed with 1 M NaOH, water, 1 M HCl, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum to an orange oil
  5. additionThe oil was treated with ethyl ether
  6. temperaturecooled in an ice bath
  7. filtrationthe precipitated product was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4bc825cd78374e75817ea559babc00f8
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05304644

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