2-Bromomethylnaphthalene → HCID 20080626, compound

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Reaction Steps

2-Bromomethylnaphthalene was reacted with methyl 5-iodosalicylate using the procedure described in Example 1 to give methyl 5-iodo-2-(naphth-2-ylmethoxy)benzoate in 68% yield. Using conventional procedures the ester was hydrolysed with base to give the corresponding acid, the acid chloride was prepared by reaction with thionyl chloride and the acid chloride was reacted with ethanolic ammonia to give 5-iodo-2-(naphth-2-ylmethoxy)benzamide in 84% yield from the ester, m.p. 163° C. The benzamide was converted to the corresponding benzonitrile in 72% yield, m.p. 108°-110° C., using the conditions described below in Example 27.

Provenance & Evidence