Ethyl bromoacetate → Ethyl [(3,5-dichloro-6-fluoropyridin-2-yl)oxy]acetate

HRID 1448405Notes

Reaction equation

HRID 1448405 reaction equation
[Na].[Cl:2][C:3]1[C:4]([OH:11])=[N:5][C:6]([F:10])=[C:7]([Cl:9])[CH:8]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:4]1[C:3]([Cl:2])=[CH:8][C:7]([Cl:9])=[C:6]([F:10])[N:5]=1)[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545SodiumHCID 178517852HCID 178517852, compound

Product 1

HCID 21522711Ethyl [(3,5-dichloro-6-fluoropyridin-2-yl)oxy]acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution was prepared by dissolving 6.9 grams (0.3 mole) of sodium metal in 700 milliliters of 95 percent ethanol. To this solution was added with stirring 54.5 grams (0.3 mole) of 3,5-dichloro-6-fluoro-2-pyridinol. Thereafter 58.5 grams (0.35 mole) of ethyl bromoacetate was added and the mixture refluxed for 5 hours. At the completion of the reaction, the ethanol was distilled off and the residue poured into water. The solid which precipitated was filtered off and taken up in hexane and dried with activated carbon and anhydrous sodium sulfate. The mixture was filtered and the hexane removed and the ethyl-(3,5-dichloro-6-fluoro-2-pyridyloxy) acetate product was recovered by distillation. The product was a white waxy solid which boiled at 135°-170° C. (M.P. 63.5°-64° C.)

Workup

  1. customA solution was prepared
  2. additionTo this solution was added
  3. temperaturethe mixture refluxed for 5 hours
  4. customAt the completion of the reaction
  5. distillationthe ethanol was distilled off
  6. additionthe residue poured into water
  7. customThe solid which precipitated
  8. filtrationwas filtered off
  9. dry with materialdried with activated carbon and anhydrous sodium sulfate
  10. filtrationThe mixture was filtered
  11. customthe hexane removed
  12. distillationthe ethyl-(3,5-dichloro-6-fluoro-2-pyridyloxy) acetate product was recovered by distillation

Sources & evidence

ORD record
ord-d65b220537904d2ca8effe6c36555f77
Source dataset
uspto-grants-1979_12
Patent number
US04180395

Reaction notes

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