4-Fluorothiophenol → 1-(4-Fluoro-phenylsulfanyl)-4-methyl-2-nitro-benzene

HRID 607234Notes

Reaction equation

HRID 607234 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=2[N+:16]([O-:18])=[O:17])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 677894-FluorothiophenolHCID 713468894-Methyl-2-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 602047941-(4-Fluoro-phenylsulfanyl)-4-methyl-2-nitro-benzene

Procedure

The product from Example 6a (5.00 g, 17.53 mmol) was reacted with 4-fluorothiophenol (2.24 g, 17.53 mmol) in place of thiophenol following the procedure from Example 5H for 18 h giving 1-(4-Fluoro-phenylsulfanyl)-4-methyl-2-nitro-benzene which was purified by silica gel column chromatography eluting with 5% EtOAc/hexane providing a solid (3.39 g, 74%). 1-(4-Fluoro-phenylsulfanyl)-4-methyl-2-nitro-benzene was reduced with SnCl2 following the procedure from Example 5I giving 2-(4-Fluoro-phenylsulfanyl)-5-methyl-phenylamine.

Sources & evidence

ORD record
ord-f061ab212f004cb692332616f31dee97
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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