2-Bromomethylnaphthalene → HCID 20080626, compound

HRID 1534615Notes

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-829ab12a8832439eaa2dd0647ee95e81
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05089513

Reaction notes

Loading…