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DOI: 10.1055/sos-SD-013-01452

Brigas, A. F.Science of Synthesis, (200413898.

Substitution of halogens, particularly of chlorine, is widely used in the synthesis of tetrazoles.[‌1‌,‌3‌,‌5‌,‌6‌] The nucleophile can be hydroxide, alkoxide, phenoxide, amine, hydrazines, thiols, or sulfonates. For example, azide ion in a heated solution of 5-chloro-1-phenyltetrazole gives the 5-azido compound in 77% yield.[‌143‌] Displacement of a 1-substituted 5-halotetrazole proceeds much more readily than that of the corresponding 2-substituted analogue and is more commonly encountered, probably because the former are more widely available.