Hydrochloric Acid → 5-(5-Chloro-2-benzoxazolyloxy)-2nitrobenzoic acid

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Reaction Steps

A reactor is charged with 1.69 grams (0.01 mole) of 5-chlorobenzoxazol-2-one (Formula II Compound), 10 milliliters of dimethylsulfoxide, and 2.76 grams (0.02 mole) of anhydrous potassium carbonate. To this mixture is added 1.85 grams (0.01 mole) of 5-fluoro-2-nitrobenzoic acid (Formula III Compound) in 4 milliliters of dimethylsulfoxide. After stirring at about 75° C. to 80° C. for about 18 hours, the reaction mixture is stripped of solvent and the residue is dissolved in a mixture of methylene chloride and water. The mixture is acidified to pH 2 to 3 with 5 normal hydrochloric acid and the aqueous phase is extracted with methylene chloride. The combined organic phases are washed with water and saturated sodium chloride solution. Filtration and removal of solvent affords 5-(5-chloro-2-benzoxazolyloxy)-2nitrobenzoic acid. (Formula IV Compound);

Provenance & Evidence