p-Chlorothiophenol → HCID 15050275, compound

Participants

Reaction Steps

To a mixture of 4-chlorobenzenethiol (1.75 g, 12.15 mmol) and K2CO3 (3.36 g, 24.30 mmol) in DMF (40 mL) was added ethyl 4-chloro-3-oxobutanoate (2.0 g, 12.15 mmol). The mixture was stirred at RT for 18 hours, diluted with saturated NaHCO3 (40 mL) and extracted with EtOAc (50 mL). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient, using LC-MS to identify fractions containing the desired product) to afford ethyl 4-(4-chlorophenylthio)-3-oxobutanoate 10A (2.07 g, 59% yield). 1H NMR (500 MHz, Chloroform-D) δ ppm 7.22-7.32 (4H, m), 4.18 (2H, q, J=7.15 Hz), 3.79 (2H, s), 3.62 (2H, s), 1.27 (3H, t, J=7.01 Hz).

Provenance & Evidence