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

HRID 1465145

Reaktionsgleichung

Reaktionsgleichung von HRID 1465145
[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, 1 H), 7.04 (d, J=8.8 Hz, 1 H), 6.10 (s, 1 H), 6.01 (d, J=8.4 Hz, 1 H), 5.58 (br s, 2 H).

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-9bc1190c9db6445e97aefee3c3043a73
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999976B2

Verknüpfte Notizen

Wird geladen…