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

HRID 2356325Notes

Reaction equation

HRID 2356325 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-5e18d2603ed14553ab6c32f05e8c5d31
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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