2-Bromopyridine → Benzyl 2-(benzyloxy)-4-(pyridin-2-yl)benzoate

Participants

Reaction Steps

Water (1.1 mL), 2-bromopyridine (0.11 mL), sodium carbonate (0.21 g), and bis(triphenylphosphine)palladium(II) dichloride (14 mg) were added to a solution of ethylene glycol dimethyl ether (3.5 mL) of the obtained benzyl 2-(benzyloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. After cooling the reaction mixture to room temperature, 2-bromopyridine (0.11 mL), sodium carbonate (0.21 g), and bis(triphenylphosphine)palladium(II) dichloride (14 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-80% hexane/ethyl acetate] to obtain 0.18 g of benzyl 2-(benzyloxy)-4-(pyridin-2-yl)benzoate.

Provenance & Evidence