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

反応式

[Na].[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N+]([O-])=O)=[N:7][CH:8]=1.[CH3:12][O:13][CH2:14][CH2:15][OH:16]>>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([O:16][CH2:15][CH2:14][O:13][CH3:12])=[N:7][CH:8]=1

参加物

反応物 3

HCID 80192-Methoxyethanol2 回

HCID 8176205-Bromo-2-nitropyridine

HCID 5360545Sodium

生成物 1

HCID 225027175-Bromo-2-(2-methoxyethoxy)pyridine収率 86%

実験手順

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)+.