Ethyl propiolate → HCID 54166829, compound

HRID 2049840Notes

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[F:8][C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1>>[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH:3]=[CH:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 12182Ethyl propiolate

HCID 677894-Fluorothiophenol

Product 1

HCID 54166829HCID 54166829, compound

Procedure

Using Example 15 procedures, ethyl propiolate and 4-fluorobenzenethiol are reacted, yielding ethyl 3-(4-fluorophenylthio)-2-propenoate. Three equiv. of this is then combined with 1 equiv. of phenyl(trifluoromethyl)mercury and 3 equiv. of dry powdered sodium iodide. This mixture is refluxed in benzene for 15-20 hr, then filtered and solvent is removed to give ethyl 3-(4-fluorophenylthio)-2,2-difluorocyclopropanecarboxylate.

Workup

customare reacted

Sources & evidence

ORD record: ord-61d5cda184f049339b20d5b29b0a324d
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04198527

Reaction notes

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