GENERAL STEPS: In a dry 250 mL round-bottomed flask equipped with a stir bar, septum and temperature probe, 1.6 M hexane solution of n-butyllithium (31.2 mL, 50 mmol) was added. The reaction system was cooled to -76 °C in a dry ice-acetone bath. Subsequently, THF (30 mL) was added to the reaction vial and a solution of 2,6-dibromopyridine (11.5 g, 50 mmol) in THF (60 mL) was added slowly dropwise by syringe, controlling the reaction temperature below -60 °C. Stirring of the dark yellow-brown solution was continued in a dry ice bath for 30 min, and then acetone (6 mL, 80 mmol) was added. The reaction mixture was stirred in a dry ice bath for 15 minutes and then slowly warmed to room temperature. After 1 hour of reaction, the reaction was quenched by careful addition of 5% aqueous ammonium chloride solution (50 mL). The reaction mixture was extracted with dichloromethane, the organic phases were combined and the solvent evaporated to give 2-(6-bromopyridin-2-yl)propan-2-ol (10.6 g, 98% yield) as an orange oil. The mass spectrum (MS) showed m/z: 216 and 218 (M+H)+.
