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

HRID 1465145

Reaction equation

HRID 1465145 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, 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).

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-9bc1190c9db6445e97aefee3c3043a73
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Linked notes

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