General procedure for the synthesis of tert-butyl 2-(3-bromophenyl)acetate: 1-bromo-3-iodobenzene (1.0 mmol), CuI (9.5 mg, 0.05 mmol), 2-pyridinecarboxylic acid (12 mg, 0.10 mmol), and cesium carbonate (978 mg, 3.0 mmol) were added to a Schlenk tube. The reaction tube was evacuated and displaced three times with argon, followed by the addition of tert-butyl acetoacetate (2.0 mmol) and 1,4-dioxane (2 mL). The reaction tube was placed in an oil bath and the reaction mixture was stirred at the indicated temperature for 33-48 hours. After completion of the reaction, the mixture was cooled and partitioned with ethyl acetate and saturated NH4Cl solution. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent petroleum ether/ethyl acetate (20:1 to 3:1) to afford the target product tert-butyl 2-(3-bromophenyl)acetate.
