The Phosphorylation of Alcohols by the Reaction of Monobromocyano-acetamide with Monobenzyl Phosphite or Inorganic Phosphorous Acid

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Abstract
This paper describes a successful method of preparing monoalkyl phosphates by the reaction of monobromocyanoacetamide with monobenzyl phosphite or inorganic phosphorous acid in the presence of alcohols. When equimolar amounts of monobromocyanoacetamide and either of the above-mentioned phosphorus compounds in alcohols were heated at about 100°C, the corresponding monoalkyl dihydrogen phosphates were obtained as anilinium salts in fairly good yields, together with cyanoacetamide and benzyl bromide or hydrogen bromide. The reaction can be interpreted in terms of a mechanism in which the initially-formed enol-phosphonium salts of cyanoacel amide are easily transformed to the second phosphonium salts by the action of the alcohols present from the salts, alkyl dihydrogen phosphates are produced.

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