Phenylacetylene → Benzene, iodoethynyl-

HRID 654609Notes

Reaction equation

HRID 654609 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC([I:28])(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[I:28][C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 10821Phenylacetylene2×HCID 677331,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexaneHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 99382Benzene, iodoethynyl-Yield 55.3%

Procedure

In a 10 mL round-bottom flask, 1.02 g of phenylacetylene (10 mmol), 4.46 g of perfluoro-n-hexyl iodide (10 mmol), and 300 mg of tetra-n-butylammonium fluoride trihydrate (0.948 mmol) were mixed at 24° C. for 1 h. Gas chromatographic analysis of the resulting mixture showed that it contained 1.26 g of 1-iodo-2phenylacetylene (55% yield) and 0.45 g of unconverted phenylacetylene.

Sources & evidence

ORD record
ord-4dd0112ef71b4798bf8259f7c69f333c
Source dataset
uspto-grants-1992_07
Patent number
US05132475

Reaction notes

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