Allyl bromide → HCID 19800641, compound

Participants

Reaction Steps

A mixture of 4-hydroxy-α-isopropyl-α-methyl-1,3-dioxo-2-isoindolineacetonitrile (25.5 g, 0.099 mol), potassium carbonate (75.0 g, 0.543 mol) and acetone is stirred for 4 hours at reflux temperature under a nitrogen atmosphere, cooled to room temperature and treated with allyl bromide (34.1 mL, 0.395 mol). The reaction mixture is stirred overnight at reflux temperature, cooled to room temperature and filtered. The filtrate is concentrated in vacuo, diluted with ether, washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title product as a yellow-orange semi-solid, 26.9 g (91.5% crude yield). The sample is purified by flash chromatography (silica gel, CH2Cl2) to afford a colorless solid, mp 54°-58° C.

Provenance & Evidence