2-Bromo-4-nitroanisole → HCID 22473552, compound

Participants

Reaction Steps

2-Bromo-4-nitroanisole (3.0 g, 12.9 mmol) was reacted with pyridine-3-boronic acid-1,3-propanediol cyclic ester (2.53 g, 15.5 mmol) over 8 hours, as described in Example 62. The resulting crude residue was purified by column chromatography on silica, using 60-70% diethyl ether in dichloromethane as the eluent, to yield 3-(2-methoxy-5-nitrophenyl)pyridine (2.26 g, 85%): δH (360 MHz, d6-DMSO) 3.94 (3H, s), 7.39 (1H, d, J 9.2), 7.50 (1H, dd, J 7.9 and 4.8), 7.97 (1H, dt, J 8.0 and 1.9), 8.19 (1H, d, J 2.8), 8.33 (1H, dd, J 9.2 and 2.8), 8.57-8.64 (1H, m), 8.74 (1H, d, J 1.9).

Provenance & Evidence