1,2-Dibromoethane → 1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethoxy)-

Reaction equation

[Br:1][CH2:2][CH2:3]Br.[OH:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16]>>[Br:1][CH2:2][CH2:3][O:5][N:6]1[C:10](=[O:11])[C:9]2[C:8](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]1=[O:16].[BrH:1].[Br:1][CH2:2][CH2:3][O:5][NH2:6]

Participants

Reactant 2

HCID 78391,2-Dibromoethane

HCID 10665N-Hydroxyphthalimide

Product 2

HCID 1998751H-Isoindole-1,3(2H)-dione, 2-(2-bromoethoxy)-

HCID 19077315O-(2-bromoethyl)hydroxylamine hydrobromide

Procedure

2-(2-Bromo-ethoxy)-isoindole-1,3-dione is prepared from 1,2-dibromoethane and N-hydroxyphtalimide as described in WO 0018790, and is then subjected to the procedure in J. Org. Chem. 1963, 28, 1604 to yield the desired product.

Sources & evidence

ORD record: ord-2f9e2f8b1443419e9b61bb11e4ee2620
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842816B2

Reaction notes

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