2-Bromo-5-nitrophenol → 5-Amino-2-trifluoromethyl-phenol

HRID 383409

Reaktionsgleichung

Reaktionsgleichung von HRID 383409
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[C:8]([OH:10])[CH:9]=1)([O-])=O.BrC1C=CC([N+]([O-])=O)=CC=1O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:12])([F:13])[F:14])=[C:8]([OH:10])[CH:9]=1

Komponenten

5

Edukt 2

HCID 128671362-Bromo-5-nitrophenolHCID 219595865-Nitro-2-(trifluoromethyl)phenol

Produkt 1

HCID 159190985-Amino-2-trifluoromethyl-phenolAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-nitro-2-(trifluoromethyl)phenol and 2-bromo-5-nitrophenol (10 g, crude) in MeOH (60 mL) was added Raney Ni (2 g) under an atmosphere of nitrogen. The mixture was stirred under hydrogen atmosphere (1 atm) at r. t. for 4 h. The catalyst was filtered off through the celite pad and the filtrate was evaporated under vacuum. The crude product was purified by preparative HPLC to obtain 5-amino-2-(trifluoromethyl)phenol (1.7 g, 11% yield for 3 steps). 1H-NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1H), 7.04 (d, J=8.8 Hz, 1H), 6.10 (s, 1H), 6.01 (d, J=8.4 Hz, 1H), 5.58 (br s, 2H).

Aufarbeitung

  1. filtrationThe catalyst was filtered off through the celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-585f86a3c2f54ed18c2c79c9b9085342
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367660B2

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