Acetone → 2-(5-Bromopyridin-2-yl)propan-2-ol

Participants

Reaction Steps

2,5-Dibromopyridine (5 g, 0.021 mol) was dissolved in toluene (100 mL). The mixture was cooled to −78° C. n-Butyllithium (2.5M solution in hexane, 8.44 mL, 0.021 mol) was added dropwise. The mixture was stirred for 30 minutes, followed by the addition of acetone (10 mL). The mixture was stirred for 45 minutes, then allowed to warm to room temperature for 1 h. The mixture was washed with 5% aqueous ammonium chloride solution (100 mL), water (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (0 to 10% ethyl acetate in heptanes) to afford the title compound (2.21 g, 48%) as a yellow oil. δH (500 MHz, CDCl3) 8.57 (d, J 2.1 Hz, 1H), 7.81 (dd, J 8.4, 2.3 Hz, 1H), 7.31 (d, J 8.4 Hz, 1H), 4.41 (s, 1H), 1.53 (s, 6H).

Provenance & Evidence