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

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

Reactant 4

HCID 79732-Bromopyridine

HCID 8434Ethylparaben

HCID 11430Potassium Carbonate

HCID 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.