Water → 2-Bromo-4-fluoro-6-nitroaniline

HRID 54313

Reaktionsgleichung

Reaktionsgleichung von HRID 54313
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:12][C:7]1[C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=[C:2]([F:1])[CH:8]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 677694-Fluoro-2-nitroaniline

Produkt 1

HCID 2920042-Bromo-4-fluoro-6-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

6-Bromo-4-fluoro-2-nitroaniline was prepared using an adaptation of the method of Mitchell et al., J. Org. Chem. 44:4733 (1979). To a solution of 4-fluoro-2-nitroaniline (500 mg, 3.2 mmol) in dry DMF (16 mL) under N2 was added dropwise a solution of N-bromosuccinimide (570 mg, 3.2 mmol) in dry DMF (16 mL). The reaction was allowed to stir 24 h. The solution was then poured into 100mL H2O and this aqueous phase extracted with 4×25 mL CH2Cl2. The combined organic phases were washed with 3×4 mL H2O and dried (MgSO4). The MgSO4 was vacuum filtered and the solvent rotary evaporated to yield a brown oil which crystallized on standing. 642 mg (85.4%). 1H NMR (CDCl3) δ6.51 (br s, 2H NH2), 7.58 (dd, JH4-3 =3 Hz, JH4-F =6.5 Hz, H-4), 7.92 (dd, JH3-4 =3 Hz, JH3-F =8.7 Hz, H-3).

Aufarbeitung

  1. extractionthis aqueous phase extracted with 4×25 mL CH2Cl2
  2. washThe combined organic phases were washed with 3×4 mL H2O
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent rotary evaporated
  6. customto yield a brown oil which
  7. customcrystallized

Quellen und Nachweise

ORD-Eintrag
ord-2c127c3d76424c8c9494c46b0a7809bd
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622952

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