Synthesis of Carboxylic Acid from Aryl Halide and Carbon Monoxide Catalyzed by Nickel Carbonyl

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Abstract
In the reacion of aryl bromide with carbon monoxide in the presence of water and a catalytic amount of nickel carbonyl, it has been found that aromatic carboxylic acids (benzoic acid, polymethylbenzoic acid, α-naphthoic acid, etc.) are formed in very high yields when such salts of carboxylic acids as potassium acetate or sodium benzoate are added to the starting materials. The carbonylation reaction of aryl bromide is strongly inhibited by the hydrobromic acid formed, and the addition of the salt of carboxylic acid effectively decreases its concentration in the course of the reaction. When the amount of potassium acetate is larger than that of aryl bromide, the rate of the carbonylation reaction of bromobenzene to form benzoic acid is proportional to the amounts of bromo-benzene, nickel tetracarbonyl, and water and to the reciprocal of the carbon monoxide pressure. From these kinetic data, the effect of the salts of carboxylic acids and the course of the reaction are discussed.