Benzyl Bromide → 3-(Benzyloxy)-6-chloro-2-iodopyridine

Participants

Reaction Steps

6-Chloro-2-iodo-3-pyridinol (1.28 g, 5 mmol) and silver carbonate (1.52 g, 5.5 mmol) were dissolved in toluene (25 ml) and benzyl bromide (654 μl, 5.5 mmol) added. The mixture was heated to reflux under nitrogen for 1 hour. After cooling, the mixture was filtered, washed with water (×2), dried (MgSO4) and evaporated to an orange oil which was flash chromatographed eluting with 5% ethyl acetate in isohexane to give the title compound as an oil which crystallised on standing. LC/MS t=3.70, [MH+] 346, 348.

Provenance & Evidence