Sodium Carbonate → HCID 70011311, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-bromo-phenyl)-acetic acid tert-butyl ester (678 mg, 2.5 mmol), bis(pinacolato)diboron (698 mg, 2.75 mmol), potassium acetate (736 mg, 7.5 mmol) and DMF (15 mL) was added PdCl2(dppf) (61 mg, 0.75 mmol). After evacuating and refilling with nitrogen three times, the reaction was heated to 80° C. for 2 h. After cooling to room temperature, methyl 2-bromo-benzoate (1.08 g, 5.0 mmol), 2M Na2CO3 aqueous (6.25 mL) and PdCl2(dppf) (61 mg, 0.75 mmol) was added to the reaction.). After evacuating and refilling with nitrogen three times again, the reaction was heated to 80° C. for 14 h. After cooling to room temperature, the mixture was poured into water (15 mL) and extracted with ether (3×25 mL). The combined organic layers were washed with water (3×25 mL), brine, dried (magnesium sulfate), and concentrated. The title compound was isolated in 22% yield as an oil following chromatography on silica gel utilizing ethyl acetate/hexane as solvent.

Provenance & Evidence