2-Tert-butyl-4-bromo-5-nitrophenol → 2-Tert-butyl-4-bromo-5-amino-phenol

HRID 74010Notes

Reaction equation

HRID 74010 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([N+:12]([O-])=O)=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([NH2:12])=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 574702362-Tert-butyl-4-bromo-5-nitrophenol

Product 1

HCID 574702482-Tert-butyl-4-bromo-5-amino-phenolYield 70%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-4-bromo-5-nitrophenol (C-14-a) (12 g, 43.8 mmol) in MeOH (90 mL) was added Ni (2.4 g). The reaction mixture was stirred under H2 (1 atm) for 4 h. The mixture was filtered and the filtrate was concentrated. The crude product was recrystallized from ethyl acetate and petroleum ether to give 2-tert-butyl-4-bromo-5-amino-phenol (C-27) (7.2 g, 70%). 1H NMR (DMSO-d6) δ 9.15 (s, 1H), 6.91 (s, 1H), 6.24 (s, 1H), 4.90 (br s, 2H), 1.22 (s, 9H); ESI-MS 244.0 m/z (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-2f65493029c44c919174f8c8a75f400c
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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