N-Iodosuccinimide → HCID 89645354, compound

HRID 70004Notes

Reaction equation

HRID 70004 reaction equation
[CH:1]1([S:4]([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)C(O)=O)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C1C(=O)N([I:24])C(=O)C1>>[CH:1]1([S:4]([CH:7]([I:24])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 120273N-IodosuccinimideHCID 89645031alpha-(Cyclopropylsulfonyl)phenylacetic acid

Product 1

HCID 89645354HCID 89645354, compoundYield 32%

Procedure

However, the use of these reagents as source of iodine for reactions of iodo-de-carboxylation are limited. Reaction of N-halosuccinimides with aryl acrylic and aryl propiolic acids gives 1-halo-2-aryl-1-alkenes and 1-halo-2-aryl-1-alkynes (J. Org. Chem. 2002, v. 67, 7861; J. Org. Chem. 1999, v. 64, 6896; J. Org. Chem. 1997, v. 62, 199; Tetrahedron 2000, v. 56, 1369). All the reactions occur in the presence of catalyst. Reaction of α-(cyclopropylsulfonyl)phenylacetic acid with NIS gives α-iodobenzyl cyclopropyl sulfone only with 32% yield (J. Org. Chem. 1974, v. 39, 2516).

Sources & evidence

ORD record
ord-ebea337bce0c441ab30dcbb724572369
Source dataset
uspto-grants-2014_09
Patent number
US08822516B2

Reaction notes

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