Ethoxalyl chloride → Ethyl 2-(3-chloro-4-(methylthio)phenyl)-2-oxoacetate

Participants

Reaction Conditions

Reaction Steps

A solution of aluminum trichloride (34.8 g, 261.4 mmol) in chloroform (120 mL) cooled to 0° C. was treated with a solution of ethyl chlorooxoacetate (18.7 mL, 167.5 mmol) in chloroform (120 mL). The mixture was stirred at 0° C. for 30 min. At this time, a solution of 2-chlorothioanisole (25.0 g, 156.5 mmol) in chloroform (120 mL) was added dropwise to the reaction mixture. It was then allowed to warm to 25° C. and stirred for an additional 3.5 h at 25° C. At this time, the reaction was quenched by the slow addition of water (500 mL) and extracted with chloroform (3×50 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded (3-chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (31.37 g, 77%) as a yellow oil: EI-HRMS m/e calcd for C18H24Cl2N2O3 (M+) 386.1164, found 386.1154.

Provenance & Evidence