Stannous Chloride → 5-Bromo-2-(phenylthio)benzenamine

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:15]([O-])=O)[CH:3]=1.Cl[Sn]Cl>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([NH2:15])[CH:3]=1

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 14531509(4-Bromo-2-nitrophenyl)(phenyl)sulfane

Product 1

HCID 284015215-Bromo-2-(phenylthio)benzenamineYield 100%

Procedure

The product from Example 121b (2.0 g, 6.45 mmol) was reduced with SnCl2 following the procedure from Example 1f giving the title compound as a clear oil (1.8 g, 100%).

Sources & evidence

ORD record: ord-b8f9331a2db64dbc9c19a379aaa0312c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338605B2

Reaction notes

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