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

HRID 471979Notes

Reaction equation

HRID 471979 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3aacce145daa4f7c83cc6d2e2595fa89
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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