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

Temperature

-78 °C

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).

1. customthe temperature below −78° C
2. customThe reaction mixture was quenched with water (50 mL)
3. extractionThe aqueous mixture was extracted with dichloromethane (2 times)
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. concentrationconcentrated in vacuo

ORD record

ord-643f0682ba7a4f208fb79cd8fbbfdcfd

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181273B2