Thionyl Chloride → Chloro-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester

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Reaction Steps

To a solution of the hydroxy-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester of Step 2 (1.0 eq) in CH2Cl2 (0.2M) was added SOCl2 (5 eq). The resulting mixture was stirred at room temperature for 12 h, poured in saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9.5:0.5) afforded the desired compound as a yellow solid.

Provenance & Evidence