2,6-Dibromopyridine → 2-(6-Bromo-2-pyridyloxy)acetic acid methyl ester

HRID 1756331Notes

Reaction equation

HRID 1756331 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:8])[CH2:6][OH:7].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=1>CN(C)C=O>[CH3:3][O:4][C:5](=[O:8])[CH2:6][O:7][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([Br:9])[N:11]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 66774Methyl Glycolate

Product 1

HCID 156617352-(6-Bromo-2-pyridyloxy)acetic acid methyl esterYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A suspension of 178 mg of sodium hydride (80% dispersion in mineral oil) in 4 ml of dimethylformamide is mixed under argon atmosphere, stirring and ice cooling with a solution of 361 mg of glycolic acid methyl ester in 2 ml of dimethylformamide and stirred for 3 hours at room temperature. Then, a solution of 948 mg of 2,6-dibromopyridine in 2 ml of dimethylformamide is added under ice cooling and the mixture is stirred for 48 hours at room temperature. The reaction mixture is poured on ice and extracted with ethyl acetate. The organic phase is washed 4 times with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. 790 mg of 2-(6-bromo-2-pyridyloxy)-acetic acid methyl ester is obtained as oily crude product.

Workup

  1. additionis mixed under argon atmosphere
  2. stirringthe mixture is stirred for 48 hours at room temperature
  3. additionThe reaction mixture is poured on ice
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed 4 times with saturated common salt solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5618f266a52b426295b91099b8e5c497
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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