Carbon tetrabromide → HCID 58105214, compound

Participants

Reaction Steps

t-Butyl 3-(6-hydroxymethylpyridin-2-yl)propionate (16.13 g) was dissolved in 200 mL of dry methylene chloride, and 33.8 g of carbon tetrabromide was added to the above solution, additionally 21.5 g of triphenylphosphine was added thereto in small portions under stirring at ice temperature, and then the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was transferred to a separating funnel, washed with saturated aqueous sodium bicarbonate, then brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue, 200 mL of a mixture of hexane-ethyl acetate (2:1) was added, the insoluble portion precipitated was filtrated off, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (hexane-ethyl acetate=5:1) to give 14.12 g of t-butyl 3-(6-bromomethylpyridin-2-yl)propionate as a light yellow oil.

Provenance & Evidence