2-Bromo-4-chloro-6-nitrophenol → 2-Amino-6-bromo-4-chlorophenol

HRID 840187Notes

Reaction equation

HRID 840187 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[OH:12].[H][H]>C(OCC)(=O)C.[Ni]>[NH2:9][C:4]1[C:3]([OH:12])=[C:2]([Br:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1

Participants

5

Reactant 2

HCID 2918712-Bromo-4-chloro-6-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 155210892-Amino-6-bromo-4-chlorophenolYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4-chloro-6-nitro-phenol (16.27 g, 64.4 mmol) in ethyl acetate (160 ml) was hydrogenated, at room temperature, with Raney-nickel (6 g). After hydrogen uptake (approx. 4.8 l) was complete, the nickel was removed by filtration and the filtrate evaporated in-vacuo to give 14.19 g (99.0%) of the title compound which was suitable for the next step.

Workup

  1. customthe nickel was removed by filtration
  2. customthe filtrate evaporated in-vacuo

Sources & evidence

ORD record
ord-fb2b0f968a914d05a270c75cc2807aa7
Source dataset
uspto-grants-2002_04
Patent number
US06365606B1

Reaction notes

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