Ethyl Glycolate → Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate

HRID 1509271Notes

Reaction equation

HRID 1509271 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].[Br:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:14](Cl)=[N:15][CH:16]=1>O1CCOCC1>[Br:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:14]([O:5][CH2:4][C:3]([O:7][CH2:8][CH3:9])=[O:6])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 12184Ethyl Glycolate2×HCID 24758Sodium hydride2×HCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 4647502Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of sodium hydride (5.31 g, 133 mmol) in 1,4-dioxane (250 ml), ethyl glycolate (12.56 ml, 133 mmol) was added drop wise over a period of 30 minutes ensuring that the temperature was maintained below 30° C. The resulting thick suspension was stirred at room temperature for 15 minutes. In a separate 11 round-bottomed flask was added 5-bromo-2-chloro-3-nitropyridine (21 g, 88 mmol) in 1,4-dioxane (150 ml) to give a brown solution. The suspension of sodium hydride and ethyl glycolate was added drop wise over a period of 30 minutes at 0° C. The resulting reaction mixture was heated to 80° C. overnight.

Workup

  1. additionwas added drop wise over a period of 30 minutes
  2. temperaturewas maintained below 30° C
  3. customIn a separate 11 round-bottomed flask
  4. customto give a brown solution
  5. additionwas added drop wise over a period of 30 minutes at 0° C
  6. customThe resulting reaction mixture
  7. temperaturewas heated to 80° C. overnight

Sources & evidence

ORD record
ord-0def8239f50143d78914e19041896930
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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