Allyl bromide → 2-Chloro-3-(1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine

Participants

Reaction Steps

A solution of 2-chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine (3.6 g, 12 mmol) in 24 mL of N,N-dimethylformamide at 0° C. is treated with 480 mg (60% in oil, 12 mmol) of sodium hydride and stirred at room temperature for 1 h. The reaction is treated with 1.14 g (13.2 mmol) of allyl bromide and stirred for 2 h. The mixture is poured into 125 mL of ethyl acetate and washed with 4×50 mL of saturated sodium chloride, 2×25 mL of 50% saturated sodium carbonate and dried over potassium carbonate. The dried organics are concentrated in vacuo, diluted with 20 mL of hexanes, and chilled to -15° C. The solid is filtered to provide 3.61 g (89%) of 2-chloro-3-(1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine.

Provenance & Evidence