Hydrochloric Acid → 2',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid

Participants

Reaction Steps

An equivalent of sodium iodide (165 mg, 1.1 mmol) and an equivalent of sodium hydroxide (32 mg) were added to a solution of 200 mg (0.80 mmol) of diflunisal in 5 ml of methanol. A 4% solution of sodium hypochlorite was dropwise added to the previous solution over a period of 75 min, keeping the temperature at 0-3° C. After every addition, a reddish colour was observed which quickly disappeared. It was stirred at this temperature for another hour and treated with a 20% aqueous solution of sodium thiosulphate. A 5% solution of HCl was added and it was extracted with dichloromethane. After the work-up, the product was recrystalized.

Provenance & Evidence