(4-azidophenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For example, 4-azidobenzylphosphorylcholine was made as follows: 4-aminobenzyl alcohol was treated with HCl and reacted with sodium nitrate, followed by sodium azide to yield 4-azidobenzyl alcohol. The product was recovered in 55% yield as a brown solid and purified by column chromatography. The product was characterized by NMR and IR. 4-azidobenzyl alcohol was treated with triethylamine, and 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP) was added to the solution. The resulting compound was reacted with trimethylamine to yield the final product of 4-azidobenzylphosphorylcholine. The final product was obtained as a pale brown powder in 60% yield and characterized by NMR and IR.