2-Bromopyridine → Ethyl 4-(pyridin-2-yloxy)benzoate

HRID 347672Notes

Reaction equation

HRID 347672 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>>[CH2:16]([O:15][C:13]([C:12]1[CH:18]=[CH:19][C:9]([O:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:10][CH:11]=1)=[O:14])[CH3:17]

Participants

5

Reactant 4

HCID 79732-BromopyridineHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 17859712Ethyl 4-(pyridin-2-yloxy)benzoateYield 26%

Procedure

2-Bromopyridine (1.98 mL, 20.0 mmol), ethyl 4-hydroxybenzoate (6.71 g, 40.0 mmol) and potassium carbonate (2.78 g, 20.0 mmol) were mixed and the mixture was stirred for 6 hours at 150° C. to 160° C. After allowed to stand for cooling, 20 mL of 8% aqueous solution of sodium hydroxide were added to the reaction mixture, which was extracted with diethyl ether. The extracted solution was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=10:1 v/v) to obtain 1.26 g (26%) of the title compound as a colorless oil.

Workup

  1. temperaturefor cooling
  2. extractionwas extracted with diethyl ether
  3. dry with materialThe extracted solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=10:1 v/v)

Sources & evidence

ORD record
ord-06d259100c8f4572bc0f64b732c99e0f
Source dataset
uspto-grants-2007_02
Patent number
US07176204B2

Reaction notes

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