Water → 5-Bromo-2-methoxypyridine

Temperature

70 °C

A mixture of 2,5-dibromopyridine (10 g, 42.37 mmol) and NaOMe (6.86 g, 127.1 mmol) in MeOH (100 mL) was heated at 70° C. and refluxed for 10 h. The mixture was allowed to cool to room temperature, was treated with water (100 mL) and extracted with EtOAc (2×150 mL). The combined organic extracts were dried over sodium sulphate and concentrated under reduced pressure to give a pale yellow, volatile oil of 5-bromo-2-methoxypyridine (6.7 g, 84% yield), which was used without purification in the next step. 1H NMR (400 MHz, CDCl3): δ 8.19 (s, 1H), 7.62 (dd, 1H), 6.65 (d, 1H), 3.90 (s, 3H); LC-MS m/z calcd for [M+H]+ 189.96. found 190.0.

1. temperaturerefluxed for 10 h
2. temperatureto cool to room temperature
3. extractionextracted with EtOAc (2×150 mL)
4. dry with materialThe combined organic extracts were dried over sodium sulphate
5. concentrationconcentrated under reduced pressure

ORD record

ord-e0068ef8381d407682db4cc3ce8da494

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2