Allyl bromide → 3-(Allyloxy)-2-chloro-6-(hydroxymethyl)-4-iodopyridine

Participants

Reaction Steps

2-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol (C2) (7.14 g, 25.0 mmol) is dissolved in DMF (50 mL) in a dry flask under N2, sodium hydride (60% dispersion in mineral oil) (1.0 g, 25.0 mmol) is added, and the reaction is stirred for 1 h at rt. Allyl bromide (2.38 mL, 27.5 mmol) is added, and the reaction mixture is stirred 48 h at rt. The mixture is diluted with EtOAc (50 mL) and washed 4×25 mL of a 50% saturated solution of 1:1 NaCl/NaHCO3. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to a white solid. The solid is washed with hexane and dried to afford 3-(allyloxy)-2-chloro-6-(hydroxymethyl)-4-iodopyridine (C50) as a white solid (68% yield). MS (EI) for C9H9Cl/NO2, m/z: 325 (M)+.

Provenance & Evidence