General procedure for the synthesis of 2-bromo-6-tert-butylpyridine using 2,6-dibromopyridine as starting material: 2,6-dibromopyridine (50 g) was slowly added to a solution of tert-butanol (300 ml) containing potassium tert-butoxide (35.5 g). Subsequently, the reaction mixture was heated to reflux and kept for 3.5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated by rotary evaporator to remove the solvent. The concentrated residue was quenched with an appropriate amount of water and subsequently extracted with ethyl acetate. All organic phase extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated again to afford the target product 2-bromo-6-tert-butylpyridine (21.4 g, 44% yield) as a clear oil. The structure of the product was confirmed by 1H NMR (270 MHz): δ1.55 (9H, s), 6.58 (1H, d), 6.98 (1H, d), 7.33 (1H, t) ppm.
