A facile method to synthesize 3-halobenzo-heterocyclic-2-carbonyl compounds is described. Mechanistic studies suggested that a halo-cyclization process, which generated the unstable spiro-acetal transition state and readily convertible to the corresponding carbonyl compound might be involved. Diverse 3-halobenzo-heterocyclic-2-carbonyl compounds could be synthesized with up to 95 % yield in mild conditions with inexpensive starting materials.