4,6-Dibromo-2-methylpyridin-3-ol → 6-Bromo-2-methylpyridin-3-ol

Participants

Reaction Conditions

Reaction Steps

4,6-Dibromo-2-methylpyridin-3-ol (15.8 g, 59.4 mmol) was dissolved in THF (200 mL). The solution was cooled to −78° C. and n-BuLi (50 mL, 125 mmol, 2.5 M in hexane) was added dropwise keeping the temperature below −78° C. The reaction mixture was allowed to stir at that temperature for 2 hours. The reaction mixture was quenched with water (50 mL) and was neutralized with 2 N HCl. The aqueous mixture was extracted with dichloromethane (2 times). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give 6-bromo-2-methylpyridin-3-ol (10.5 g, 95%) as a yellow oil. 1H-NMR (300 MHz, DMSO) 2.29 (s, 3H), 7.08 (d, 1H), 7.26 (d, 1H), 10.08 (s, 1H).

Provenance & Evidence