2-Tert-butyl-4-bromo-5-nitrophenol → 2-Tert-butyl-4-bromo-5-amino-phenol

HRID 1804995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804995
[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([N+:12]([O-])=O)=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([NH2:12])=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 574702362-Tert-butyl-4-bromo-5-nitrophenol

Produkt 1

HCID 574702482-Tert-butyl-4-bromo-5-amino-phenolAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-tert-butyl-4-bromo-5-nitrophenol (C-14-a) (12 g, 43.8 mmol) in MeOH (90 mL) was added Ni (2.4 g). The reaction mixture was stirred under H2 (1 atm) for 4 h. The mixture was filtered and the filtrate was concentrated. The crude product was recrystallized from ethyl acetate and petroleum ether to give 2-tert-butyl-4-bromo-5-amino-phenol (C-27) (7.2 g, 70%). 1H NMR (DMSO-d6) δ 9.15 (s, 1H), 6.91 (s, 1H), 6.24 (s, 1H), 4.90 (br, s, 2H), 1.22 (s, 9H); ESI-MS 244.0 m/z (MH+).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was recrystallized from ethyl acetate and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-066fde9ff0434e61831146572a6b2afd
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354427B2

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