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

HRID 1441252Notes

Reaction equation

HRID 1441252 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 refluxfor 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 at refluxfor 10 hr
  2. customThe precipitate was removed by suction filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8e81b6c0022f4062b1e2ca61826c280c
Source dataset
uspto-grants-2010_02
Patent number
US07655648B2

Reaction notes

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