Thionyl Chloride → 4'-Chlorobiphenyl-4-sulfonyl chloride

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=O)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([Cl:20])(=[O:17])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 154291414'-Chloro[1,1'-biphenyl]-4-sulfonic acid

Product 1

HCID 27947454'-Chlorobiphenyl-4-sulfonyl chlorideYield 95%

Procedure

A suspension of the 4′-chlorobiphenyl-4-sulfonic acid in 100 mL of thionyl chloride is heated at reflux for 6 h, and the resulting homogeneous solution is then cooled to RT. The mixture is concentrated under reduced pressure and the residue is triturated with diethyl ether and dried to afford 9.8 g (95%) of 4′-chlorobiphenyl-4-sulfonyl chloride as an off-white solid.

Workup

temperatureis heated
temperatureat reflux for 6 h
concentrationThe mixture is concentrated under reduced pressure
customthe residue is triturated with diethyl ether
customdried

Sources & evidence

ORD record: ord-b8add0fe30734fef9ae64c35dd7ef0ed
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277987B1

Reaction notes

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