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

Reaktionsgleichung

[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

Komponenten

Edukt 3

HCID 80192-Methoxyethanol2×

HCID 8176205-Bromo-2-nitropyridine

HCID 5360545Sodium

Produkt 1

HCID 225027175-Bromo-2-(2-methoxyethoxy)pyridineAusbeute 86 %

Versuchsvorschrift

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)+.