Ethoxalyl chloride → Ethyl [4-(cyclopropylsulfanyl)phenyl](oxo)acetate

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask was placed methylene chloride (100 mL) and aluminum trichloride (9.87 g, 74.01 mmol) and it was cooled to 0° C. in an ice bath. To this was then added dropwise chloro-oxo-acetic acid ethyl ester (6.46 mL, 58.03 mmol) keeping the temperature of the solution below 5° C. and it was then stirred for 30 min at 0° C. After this time a solution of cyclopropylsulfanyl-benzene (8.00 g, 53.24 mmol) in methylene chloride (5 mL) was added dropwise while keeping the temperature of the solution below 5° C. The ice bath was then removed and the reaction allowed to warm up to 25° C. and stirred for 3 h. The reaction was then cooled back down to 0° C. in an ice bath and added dropwise ice water (20 mL) keeping the temperature of the solution below 20° C. It was then stirred for 15 min and then transferred to a separatory funnel and separated. The organic phase was then washed with water (2×25 mL), saturated aqueous sodium bicarbonate solution (2×25 mL) and water (25 mL) and then dried over magnesium sulfate, filtered and concentrated in vacuo to afford (4-cyclopropylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (12.19 g, 91%) as a yellow oil and used without further purification.

Provenance & Evidence