Sulfuric Acid → 5-Bromo-2-acetylsalicylic acid

Participants

Reaction Steps

5-Bromosalicylic acid (100 g, 0.46 mol) and acetic anhydride (105 ml) were combined, to which 0.5 ml of concentrated sulfuric acid was added. The resulting mixture solidified in several minutes. Subsequent to suspension in 1,000 ml of water, the solid matter was collected by filtration and then washed with water. The thus-obtained white powder was dried in air and then dissolved in 1,000 ml of ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Subsequent to concentration under reduced pressure, 105 g of 2-acetoxy-5-bromobenzoic acid were obtained as white crystals (yield: 89%).

Provenance & Evidence