Diethyl Ether → Ethyl (6-bromo-2-nitropyridin-3-yloxy)acetate

HRID 1782010Notes

Reaction equation

HRID 1782010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[N:3]=1.C(=O)([O-])[O-:13].[K+].[K+].[CH3:18][CH2:19][O:20][CH2:21][CH3:22]>CC(C)=O.BrCC(OCC)=O>[Br:1][C:2]1[N:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([O:8][CH2:18][C:19]([O:20][CH2:21][CH3:22])=[O:13])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 218738086-Bromo-2-nitropyridin-3-ol

Product 1

HCID 59560649Ethyl (6-bromo-2-nitropyridin-3-yloxy)acetateYield 89%

Reagents, catalysts & solvents 2

HCID 7748Ethyl bromoacetateCatalystHCID 180AcetoneSolvent

Procedure

The hydroxypyridine (f) (30 g, 0.14 mol) was suspended in acetone (200 ml), and potassium carbonate (39 g, 0.28 mol) was added, followed by ethyl bromoacetate (15.7 ml, 0.14 mmol). The reaction was heated at reflux for 10 hours, then was cooled to room temperature and diluted with Et2O. The precipitate was removed by suction filtration, and the filtrate was concentrated in vacuo to afford material (38 g, 89%), which was used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 10 hours
  3. customThe precipitate was removed by suction filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1771243a14b444e290dbf8af8b46e80b
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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