Propanoic acid, 2-bromo-2-methyl-, ethyl ester → Ethyl 2-(acetylthio)-2-methylpropanoate

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Reaction Steps

To a solution of ethyl α-bromoisobutyrate (62 g, 0.32 mol) in N,N-dimethylformamide (500 mL) at room temperature is added potassium thioacetate (72 g, 0.63 mol). The reaction is stirred for 16 h and then concentrated under reduced pressure. The residue is diluted with a 2M aqueous hydrochloric acid solution (500 mL) and extracted with ethyl acetate (3×500 mL). The organic fractions are combined, washed with brine (300 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Purification by chromatography on silica eluting with heptanes/dichloromethane provides the title compound, m/z 191 [M+H+].

Provenance & Evidence