Ethyl bromoacetate → Ethyl 2-[2-(4-fluorobenzoyl)pyridin-3-yloxy]acetate

HRID 429204Notes

Reaction equation

HRID 429204 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[C:13]([O:14][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 229879782-(4-Fluorobenzoyl)-3-hydroxypyridine

Product 1

HCID 10881213Ethyl 2-[2-(4-fluorobenzoyl)pyridin-3-yloxy]acetateYield 102.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of give 2-(4-fluorobenzoyl)-3-hydroxypyridine (2.2 g, 11.3 mmol), ethyl bromoacetate (1.6 ml, 14.15 mmol) and potassium carbonate (4.34 g, 31.4 mmol) in acetone (40 ml) was heated at reflux. After 3 h, the reaction was cooled to room temperature, filtered and concentrated in vacuo to give ethyl 2-[2-(4-fluorobenzoyl)pyridin-3-yloxy]acetate (3.5 g) which was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cda20e115c294458aca40971cfc00fe4
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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