2-Methoxyethanol → 5-Bromo-2-(2-methoxyethoxy)pyridine

Participants

Reaction Steps

To a stirred solution of sodium (591 mg, 24.6 mmol) in 2-methoxyethanol (20 mL) was added a solution of 5-bromo-2-nitropyridine (17-1, 5.00 g, 24.6 mmol) in 2-methoxyethanol (10 mL) at room temperature. The reaction mixture was stirred at reflux for 2.5 h. The solution was concentrated and the residue was diluted with CH2Cl2 and H2O. The organic layer was dried and evaporated under reduced pressure to give 5-bromo-2-(2-methoxyethoxy)pyridine (17-2, 4.9 g) in 86% yield: 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=2.6 Hz, 1 H), 7.64 (dd, J=8.7, 2.6 Hz, 1 H), 6.72 (d, J=8.7 Hz, 1 H), 4.43 (t, J=6.6 Hz, 2 H), 3.73 (t, 2H), 3.41 (s, 3 H). ESI-MS: m/z 232.0 (M+H)+.

Provenance & Evidence