3,5-Dibromopyridine → 3-Bromo-5-methoxypyridine

Temperature

100 °C

To a solution of 3,5-dibromopyridine (10.0 g, 42.2 mmol) in DMF (10 mL) in a flask with a distillation head was added NaOMe solution 25% wt/wt (10 mL) and the mixture was heated to 100° C. for 3 hours. At the end of 3 hours ˜8 mL of MeOH was collected. The DMF solution was cooled to room temperature and diluted with H2O (25 mL) and extracted with MTBE (2×25 mL). The combined organic layers were washed with H2O (2×25 mL), dried over Na2SO4, filtered and concentrated. The residue was then dried under high vacuum for 10 hours to give the title compound (5.2 g, 66%). 1H NMR (400 MHz, DMSO-D6) δ 8.26-8.31 (m, 2H) 7.69-7.72 (m, 1H) 3.84 (s, 3H).

1. customAt the end of 3 hours ˜8 mL of MeOH was collected
2. temperatureThe DMF solution was cooled to room temperature
3. additiondiluted with H2O (25 mL)
4. extractionextracted with MTBE (2×25 mL)
5. washThe combined organic layers were washed with H2O (2×25 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was then dried under high vacuum for 10 hours

ORD record

ord-c1f1d69fdcdb4fa5bfb67749f258d6b9

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07868026B2