2,5-Dibromopyridine → 5-Bromo-2-methoxypyridine

Temperature

70 °C

A mixture of 2,5-dibromopyridine (5.5 g, 23.2 mmol) and NaOMe (3.76 g, 69.6 mmol) in MeOH (60 mL) was heated at 70° C. for 1 hour and then allowed to cool to room temperature. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give a pale yellow volatile oil (2.5 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.26 (s, 1H), 7.87 (dd, 1H), 6.81 (d, 1H), 3.82 (s, 3H).

1. temperatureto cool to room temperature
2. extractionextracted with EtOAc (2×100 mL)
3. dry with materialThe combined organic layers were dried over Na2SO4
4. concentrationconcentrated under reduced pressure

ORD record

ord-d41d340b7f244188ba66816a78bfbe29

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371316B2