Chloroacetic Acid → 7041-52-3

Participants

Reaction Conditions

Reaction Steps

A 50 mL round bottom flask equipped with a reflux condenser, thermometer and magnetic stirrer was charged with 1.6 g (13 mmol) of sodium sulfite, 4.2 g (50 mmol) of sodium bicarbonate and 20 mL of water. The resulting slurry was heated to 75° C. and 4.0 g (13 mmol) of 2-bromo-4-(chlorosulfonyl)benzoyl chloride was added over 30 minutes. After heating at 75° C. for one hour, chloroacetic acid (1.8 g, 19 mmol) and 1.0 mL (19 mmol) of 50% aqueous sodium hydroxide were added sequentially to the aqueous solution of 2-bromo-4-sulfinylbenzoic acid, and the reaction mixture heated to reflux. Additional chloroacetic acid (2.0 g) was added as necessary to drive the reaction to completion. After heating for 16 hours, the reaction mixture was allowed to cool to ambient temperature and acidified with concentrated HCl. The precipitated solids were collected by filtration and dried to give 1.6 g of 2-bromo-4-(methylsulfonyl)benzoic acid, corresponding to a 46% yield.

Provenance & Evidence