A New Method for the Phosphorylation of Alcohols by Means of Bromine and Dibenzylhydrogen Phosphite

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Abstract
Various alkyldihydrogen phosphates were obtained in good yields by reacting alcohols, dibenzylhydrogen phosphite, and bromine in the presence of triethylamine, followed by catalytic hydrogenation. When benzyl alcohol and diethyl phosphite were used in the above reaction, only the oxidation of the latter took place, giving diethylhydrogen phosphate in an excellent yield. These results suggest that the above phosphorylation of alcohol proceeds through a quaternary phosphonium salt, i. e., dibenzyloxyalkyloxyhydroxy phosphonium bromide, which is then converted into an alkylbenzylhydrogen phosphate. The effect of tertiary amines on this type of phosphorylation was also examined.

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