Thionyl Chloride → (4-Fluorophenylthio)acetyl chloride

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([Cl:15])=[O:12])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 7361972-[(4-Fluorophenyl)sulfanyl]acetic acid

Product 1

HCID 13076191(4-Fluorophenylthio)acetyl chlorideYield 88%

Procedure

A mixture of 5.3 g of (4-fluorophenylthio)acetic acid and 6.8 g of thionyl chloride is refluxed for 2 hours. Excess of thionyl chloride is evaporated in vacuo and the residue distilled. There are obtained 5.1 g (88%) of oily (4-fluorophenylthio)acetyl chloride, b.p. 76°-77° C./0.25 Torr.

Workup

temperatureis refluxed for 2 hours
customExcess of thionyl chloride is evaporated in vacuo
distillationthe residue distilled

Sources & evidence

ORD record: ord-490eada3ec7f42a4a9a4961ce81a8b3d
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04243805

Reaction notes

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