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

HRID 1820668Notes

Reaction equation

HRID 1820668 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

2-Bromo-5-hydroxy-6-nitropyridine (30 g, 0.14 mole) was suspended in acetone (200 ml), and potassium carbonate (39 g, 0.28 mole) was added, followed by ethyl bromoacetate (15.7 ml, 0.14 mmole). The reaction was heated at reflux for 10 hr, 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; MS (ES) m/z 305.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-4abbb2cacd354356b0fe49bc3192a450
Source dataset
uspto-grants-2009_10
Patent number
US07605169B2

Reaction notes

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