Acetic Acid → 3,5-Dibromo-2-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

Bromine (17.8 g, 111 mmol) was added to a solution of 5-bromo-2-methoxypyridine (12.0 g, 63.8 mmol), sodium acetate (5.23 g, 63.8 mmol), and acetic acid (65 mL). The mixture was stirred at 80° C. for 4 h and then at room temperature for 12 h. The mixture was diluted with ether and washed with water, sodium bicarbonate and hypo solution. The organic layer was dried over sodium sulphate, filtered and concentrated. Purification by chromatography using 1-5% ethyl acetate in pet ether provided 10.6 g of the desired compound: 1H NMR (300 MHz, DMSO-d6) 8.20-8.40 (m, 2H), 3.92 (s, 3H).

Provenance & Evidence