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 drop-wise keeping the temperature below −78° C. The mixture was allowed to stir at that temperature for 2 h. The mixture was quenched with water (50 mL) and was neutralized with 2 N HCl. The aqueous mixture was extracted with dichloromethane (2×). The combined organic layers were dried (Na2SO4) and concentrated 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 mixture was quenched with water (50 mL)
3. extractionThe aqueous mixture was extracted with dichloromethane (2×)
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. concentrationconcentrated

ORD record

ord-628439cd3b1c435ebcdfe4e4c535ca33

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403839B2