Hexane → 6-Bromo-2-methylpyridin-3-ol

Temperature

-78 °C

4,6-Dibromo-2-methyl-pyridin-3-ol (14.32 g, 53.65 mmol) was dissolved in tetrahydrofuran (181 mL). The solution was cooled to −78° C. and n-butyllithium in hexane (45.16 mL of 2.5 M, 112.9 mmol) was added drop-wise keeping the temperature at −78° C. The mixture was stirred for 2 hours before it was quenched with water (45 mL) and neutralized with 1 N HCl. The aqueous mixture was extracted with dichloromethane (3×100 mL). The organic layers were combined and dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield 6-bromo-2-methyl-pyridin-3-ol (9.41 g, 93%). 1H NMR (400 MHz, DMSO) δ 10.10 (s, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 2.29 (s, 3H). ESI-MS m/z calc. 187.0, found 188.3 (M+1)+; Retention time: 0.85 minutes (3 min run).

1. customat −78° C
2. customwas quenched with water (45 mL)
3. extractionThe aqueous mixture was extracted with dichloromethane (3×100 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customthe solvent was evaporated under reduced pressure

ORD record

ord-a8d8759444164182a69702fa915ecf8c

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365588B2