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

HRID 2232998Notes

Reaction equation

HRID 2232998 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-497f1afae45a488aa7d4ce081d625583
Source dataset
uspto-grants-2010_05
Patent number
US07709472B2

Reaction notes

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