Water → 4-bromo-3-fluoro-2-nitroaniline

HRID 475225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475225
[F:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:19])C(=O)C1.O>CN(C=O)C>[Br:19][C:7]1[CH:6]=[CH:5][C:4]([NH2:8])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[F:1]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 27828343-Fluoro-2-nitroaniline

Produkt 1

HCID 27831584-bromo-3-fluoro-2-nitroanilineAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 138 (25 g, 0.160 mol) in DMF (250 mL) at 0° C. was added dropwise a solution of NBS (28.5 g, 0.160 mol) in DMF (100 mL). The resulting mixture was stirred at 0° C. for 1 h and then at RT for another hour. After the completion of the reaction, the mixture was poured into water (4 L) and extracted with EtOAc. The combined organic layers were washed with water and brine solution, dried (Na2SO4), filtered and concentrated in vacuo to afford 34 g (90%) of 4-bromo-3-fluoro-2-nitro-phenylamine (140) as a yellow solid which was used without further purification.

Aufarbeitung

  1. waitat RT for another hour
  2. customAfter the completion of the reaction
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d1afc592045e4de7a4afec0886b7cbb3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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