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

Participants

Reaction Steps

2-Methoxyethanol (5.12 mL, 85.0 mmol) was dissolved in 1,4-dioxane (125 ml). Potassium tert-butoxide (7.00 g, 62.4 mmol) was added under N2. The mixture was stirred for 10 minutes. 5-Bromo-2-chloropyridine (10.0 g, 52.0 mmol) was added and the resulting mixture was refluxed for 2 hours. The mixture was poured into brine and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated to dryness. Purification by flash chromatography (silica, heptanes/EtOAc 4:1) gave the title compound as a colorless oil (8.74 g, 73%) sufficiently pure for the next step.

Provenance & Evidence