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

HRID 1805108Notes

Reaction equation

HRID 1805108 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 20%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-nitro-2-(trifluoromethyl)phenol and 2-bromo-5-nitro-phenol (10 g, 48.28 mmol) in methanol (60 mL) was added Raney Nickel (2.83 g, 318 μL, 48.28 mmol) under an atmosphere of nitrogen. The reaction mixture was then stirred for 4 h at room temperature under an atmosphere of hydrogen (1 atm). The catalyst was removed by filtration through a pad of celite 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, 20%). 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. customThe catalyst was removed by filtration through a pad of celite
  2. customthe filtrate was evaporated under vacuum
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-6a090916720c4199b106d0dc564abc7b
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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