Methanol → 2-Amino-6-bromophenol

HRID 469804Notes

Reaction equation

HRID 469804 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[OH:11])([O-])=O.CO>C1COCC1.[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[OH:11]

Participants

5

Reactant 2

HCID 887MethanolHCID 135454532-Bromo-6-nitrophenol

Product 1

HCID 155315062-Amino-6-bromophenol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5 g (22.9 mmol) 2-nitro-6-bromo-phenol (Fluka 67211) is hydrogenated in the presence of 0.1 g Ra—Ni (B113W EtOH, Degussa) in 100 ml of THF:MeOH=1:1. for 4 h. The reaction mixture is filtered (2 glass fiber filters used) and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane:EtOAc=2:1) to afford the title compound as a reddish oil which slowly solidifies.

Workup

  1. filtrationThe reaction mixture is filtered (2 glass fiber filters used)
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is purified by chromatography (silicagel, hexane:EtOAc=2:1)

Sources & evidence

ORD record
ord-991f4ad3cf6d4953aefaa3c986c6fd40
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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