Bromonitromethane → 5-(Tert-butyl)-2-nitroselenophene-3-ylamine

Reaction equation

Cl[C:2]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:3][C:4]#[N:5].[Se-2:10].[Na+].[Na+].Br[CH2:14][N+:15]([O-:17])=[O:16]>>[NH2:5][C:4]1[CH:3]=[C:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[Se:10][C:14]=1[N+:15]([O-:17])=[O:16]

Participants

Reactant 3

HCID 68423Bromonitromethane

HCID 73973Sodium selenide

HCID 27356613-Chloro-4,4-dimethylpent-2-enenitrile

Product 1

HCID 866982845-(Tert-butyl)-2-nitroselenophene-3-ylamine

Procedure

The 3-chloro-3-tert-butylprop-2-enenitrile is reacted with sodium selenide, bromonitromethane in the presence of a base to provide 3-amino-5-tert-butyl-2-nitroselenophene.

Sources & evidence

ORD record: ord-bfe6a13a769a44db92c80d1c93dc8dd7
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815879B2

Reaction notes

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