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

Participants

Reaction Steps

To a solution of 62 g (0.32 mol) of ethyl α-bromoisobutyrate in DMF (500 mL) at room temperature are added 72 g (0.63 mol) of potassium thioacetate. 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 over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography (silica, eluent heptanes, DCM) provides 44 g of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester. Yield: 73%; ES-MS: m/z 191 [M+H]; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.27 (3H, t, J=7.09 Hz), 1.58 (6H, s), 2.28 (3H, s), 4.20 (2H, q, J=7.09 Hz)

Provenance & Evidence