Methanol → 3-Bromo-2-methoxy-4-methyl-5-nitropyridine

Participants

Reaction Steps

To a solution of 3-Bromo-2-chloro-4-methyl-5-nitro-pyridine (5.00 g, 19.9 mmol) in anyhdrous Methanol was added a 25% methanolic NaOMe solution (10.7 mL, 2.5 eq). The reaction was stirred at room temperature for 24 hr. The solvent was removed under reduced pressure giving a solid. Water (100 mL) was added to the flask and the flask sonicated for 5 minutes. The precipitate was filtered and washed with water (50 mL) giving a beige powder. The aqueous mother liquor was extracted with EtOAc (1×), the organic washed with brine, and dried. The two solids were combined giving 3-Bromo-2-methoxy-4-methyl-5-nitro-pyridine (2.75 g, 10.6 mmol, 53%). 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 1H), 4.12 (s, 3H), 2.72 (s, 3H).

Provenance & Evidence