Hydrochloric Acid → 3-Bromo-5-fluoro-2-methylaniline

HRID 1689864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689864
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12].Cl>CO.C(Cl)Cl.[Fe]>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([NH2:9])[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 27733851-Bromo-5-fluoro-2-methyl-3-nitrobenzene

Produkt 1

HCID 27376413-Bromo-5-fluoro-2-methylanilineAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of crude 1-bromo-5-fluoro-2-methyl-3-nitro-benzene (5.96 g) in MeOH (90 mL) was added concentrated hydrochloric acid (11.7 mL) and iron (6.1 g) and the reaction mixture was heated to reflux. After 16 h, the mixture was cooled, diluted with DCM, washed with sodium carbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 3-bromo-5-fluoro-2-methyl-phenylamine (1.46 g).

Aufarbeitung

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturethe mixture was cooled
  3. washwashed with sodium carbonate solution
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-4232c94f0b0843988e4a70779e75d9d0
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153629B2

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