Water → HCID 14876733, compound

HRID 1943752Notes

Reaction equation

HRID 1943752 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[CH:11]=[C:12]([N+:17]([O-:19])=[O:18])[C:13](Cl)=[N:14][CH:15]=1.O>O1CCCC1>[CH3:1][O:2][C:3](=[O:6])[CH2:4][O:5][C:13]1[C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]([Br:9])=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 14876733HCID 14876733, compoundYield 117.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Hydroxy-acetic acid methyl ester (46 mg, 0.50 mmol) was dissolved in 2 ml of anhydrous tetrahydrofuran under nitrogen atmosphere, and sodium hydride (40 mg, 1.0 mmol) was added thereto at room temperature. After stirring for 30 minutes, 5-bromo-2-chloro-3-nitro-pyridine (100 mg, 0.42 mmol) dissolved in 1 ml of anhydrous tetrahydrofuran was added dropwise at room temperature, and the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction by adding water, the mixture was extracted with dichloromethane, and the organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of n-hexane:ethyl acetate=9:1. The fractions containing the product were collected and evaporated to obtain (5-bromo-3-nitro-pyridin-2-yloxy)-acetic acid methyl ester as yellow solid (144 mg, 99%).

Workup

  1. customat room temperature
  2. additionwas added dropwise at room temperature
  3. stirringthe reaction mixture was stirred at room temperature for 18 hours
  4. customAfter completion of the reaction
  5. extractionthe mixture was extracted with dichloromethane
  6. washthe organic layer was washed with water and saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica eluting with a solvent of n-hexane
  11. additionThe fractions containing the product
  12. customwere collected
  13. customevaporated

Sources & evidence

ORD record
ord-e037a389072f4e45aa6d269fceb6f634
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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