Sodium Dithionite → 4-Bromo-5-fluoro-2-methoxyaniline

HRID 432489

Reaktionsgleichung

Reaktionsgleichung von HRID 432489
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Br:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-])=O)=[CH:12][C:11]=1[F:21]>C(O)C.O>[Br:9][C:10]1[C:11]([F:21])=[CH:12][C:13]([NH2:18])=[C:14]([O:16][CH3:17])[CH:15]=1

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 223473121-Bromo-2-fluoro-5-methoxy-4-nitrobenzene

Produkt 1

HCID 223472984-Bromo-5-fluoro-2-methoxyanilineAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydrosulfite (14.7 g, 84.4 mmol) was added to a solution of 1-bromo-2-fluoro-5-methoxy-4-nitrobenzene (9.28 g, 37.12 mmol) in ethanol (180 mL) and water (130 mL) at 80° C. in three portions. After 5 hours the organic solvent was removed and the solid in aqueous layer was collected by filtration. The solid was further washed with heptane/ethyl acetate (3:2, 400 mL). The filtrate was evaporated to give 4-bromo-5-fluoro-2-methoxyaniline (3.29 g, 40%). 1H NMR (DMSO-d6) δ 3.75 (s, 3H), 5.22 (s, 2H), 6.56 (d, J=10.68 Hz, 2H), 6.94 (d, J=6.57 Hz, 2H).

Aufarbeitung

  1. customAfter 5 hours the organic solvent was removed
  2. filtrationthe solid in aqueous layer was collected by filtration
  3. washThe solid was further washed with heptane/ethyl acetate (3:2, 400 mL)
  4. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-8529a201d35649238137e69df1b8cdfb
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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