Phenylacetylene → Stk331085

HRID 65635

Reaction equation

HRID 65635 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17]>[Cu]I>[C:1]1([C:7]#[C:8][C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 113411-Bromo-2-nitrobenzene

Product 1

HCID 800027Stk331085Yield 84%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
56 °C

Procedure

Example 1 was repeated except phenylacetylene ##STR9## was employed as the sole alkyne (25 mmols); the amount of CuI was increased to 0.25 mmol; and the reaction temperature was increased to 56° C. After 24 hours, the bromonitrobenzene was totally converted, giving an 84% yield of phenyl-3-nitrophenylacetylene ##STR10## Example 16 shows that it is not predictable (when Ex. 16 is compared with Exs. 13-15) which charge stocks will react with which halogenated arenes.

Sources & evidence

ORD record
ord-3b65ac9c63ba47d7a4d85e4fa6c0c919
Source dataset
uspto-grants-1978_12
Patent number
US04128588

Linked notes

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