2-Chlorophenol → Ethyl (4-chlorosulfonyl-2-chloro-phenoxy)-acetate

Participants

Reaction Steps

A solution of 2-chlorophenol (25.7 g, 200 mmol), potassium carbonate (41.4 g, 300 mmol) and ethyl bromoacetate (35.1 g, 210 mmol) in 2-butanone (240 ml) was stirred at 100° C. for 24 h. The reaction mixture was filtered and evaporated. The residue was dissolved in toluene (100 ml), washed with water (3×25 ml), dried and evaporated. The residue (37 g, 172 mmol) was dissolved in dichloromethane (50 ml) and chlorosulfonic acid (93 g, 800 mmol) was added slowly at −10° C. The reaction mixture was stirred at room temperature for 1 h. Ice water (25 ml) was added carefully and the mixture was extracted with dichloromethane (3×100 ml). The combined organic phases were washed with water, dried and evaporated to give crude (4-chlorosulfonyl-2-chloro-phenoxy)-acetic acid ethyl ester as an oil in 47.5 g yield.

Provenance & Evidence