2-Bromomethylnaphthalene → HCID 20080626, compound

HRID 1614244Notes

Reaction equation

Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[I:13][C:14]1[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]([OH:24])=[CH:16][CH:15]=1>>[I:13][C:14]1[CH:15]=[CH:16][C:17]([O:24][CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

Reactant 2

HCID 703202-Bromomethylnaphthalene

HCID 248910Methyl 5-Iodosalicylate

Product 1

HCID 20080626HCID 20080626, compoundYield 68%

Procedure

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.

Sources & evidence

ORD record: ord-e88fbe22dd394c97b6a3e7348b64d478
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196422

Reaction notes

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