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

HRID 977576Notes

Reaction equation

HRID 977576 reaction equation
[H-].[CH3:2][O:3][C:4](=[O:7])[CH2:5][OH:6].[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1>CN(C)C=O>[CH3:2][O:3][C:4](=[O:7])[CH2:5][O:6][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([Br:8])[N:10]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 66774Methyl GlycolateHCID 166653Hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 178 mg of sodiura 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 dimethylformaraide 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-7ca406e01b0e45deaa25dfe17918443e
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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