The invention discloses a synthesis method of a benzofuro [3, 2-b]
benzofuran compound, and belongs to the technical field of
organic synthesis. According to the method, o-
hydroxybenzoate compounds or halogenated derivatives thereof and methyl bromoacetate are taken as starting raw materials, and a target product is prepared through five steps of reaction: step 1, cyclization is performed at 0 DEG C to
room temperature under an alkaline condition to obtain a
benzofuran carboxylate intermediate; 2, sulfonylating by
trifluoromethanesulfonic anhydride to obtain a
sulfonate intermediate; 3, carrying out an etherification reaction with an o-halogenated
phenol compound at the temperature of 80-120 DEG C; 4, hydrolyzing through inorganic strong base to obtain a
benzofuran carboxylic acid intermediate; and 5, carrying out intramolecular ring closing at 80-180 DEG C under the action of a
palladium catalyst and DBU. The raw materials are cheap and easy to obtain, the reaction selectivity is high, the total yield is stable, the substrate adaptability is wide, efficient synthesis of unilateral and bilateral
halogen substituted derivatives of benzofuro [3, 2b] benzofuran compounds is successfully achieved, and the method has remarkable industrial application value.