p-Chlorothiophenol → Benzene, 1-chloro-4-(propylsulfonyl)-

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:14]C1C=CC(S)=CC=1.ICCC>>[Cl:14][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7815p-Chlorothiophenol

HCID 336431-Iodopropane

HCID 142895251-Fluoro-4-(propylsulfonyl)benzene

Product 1

HCID 21041456Benzene, 1-chloro-4-(propylsulfonyl)-Yield 82%

Procedure

Following the general method as outlined in Intermediate 105, starting from 4-chlorothiophenol (Aldrich) and 1-iodopropane, the title compound was obtained as an oil which solidified upon standing in 82% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record: ord-84eb0190c2e14753b9e212dfd65a6b48
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273769B2

Reaction notes

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