Citric Acid → HCID 58508911, compound

Participants

Reaction Steps

Water (3 mL), sodium carbonate (0.76 g), 2-bromopyridine (0.42 mL), and tetrakis(triphenylphosphine)palladium(0) (0.17 g) were added to an ethylene glycol dimethyl ether (10 mL) solution of tert-butyl 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.0 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. 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 [eluent: 90-85% hexane/ethyl acetate] to obtain 0.32 g of tert-butyl 2-nitro-4-(pyridin-2-yl)benzoate as a light yellow oily substance.

Provenance & Evidence