Ethyl Acetate → Tert-butyl 2-(2-hydroxy-5-phenylbenzamido)-4-phenylbenzoate

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Reaction Steps

Ethylene glycol dimethyl ether (1.4 mL), water (0.42 mL), phenylboranic acid (0.045 g), sodium bicarbonate (0.063 g), and bis(triphenylphosphine)palladium(II) dichloride (4 mg) were added to tert-butyl 2-(2-acetoxy-5-bromobenzamido)-4-phenylbenzoate (0.15 g), followed by heating to reflux under a nitrogen atmosphere for 45 minutes. The reaction mixture was cooled to room temperature, and potassium carbonate (0.12 g) was added thereto, followed by stirring under a nitrogen atmosphere at room temperature for 2 hours. Water and ethyl acetate were added to the reaction mixture. 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. Methanol (2 mL), dioxane (4 mL), and a 2 mol/L aqueous solution of sodium hydroxide (1.5 mL) were added to the obtained residue, followed by stirring at room temperature for 1 hour and 40 minutes. The solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate were added to the residue. 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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-80% hexane/ethyl acetate] and further purified by silica gel column chromatography [eluent: chloroform] to obtain 0.086 g of tert-butyl 2-(2-hydroxy-5-phenylbenzamido)-4-phenylbenzoate as a white solid.

Provenance & Evidence