Dimethylformamide → 4-(2-phenylethynyl)aniline

HRID 1627718Notes

Reaction equation

CN(C)C=O.C(N(CC)CC)C.[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.I[C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>[Cu](I)I.C(OCC)(=O)C.O>[C:13]1([C:19]#[C:20][C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Dimethylformamide (10 ml), 10 ml of triethylamine, 0.93 g of phenylacetylene, 0.32 g of palladium chloride-ditriphenylphosphine complex, and 0.09 g of copper iodide were added to 1.0 g of 4-iodoaniline, and the mixture was stirred at 50° C. for 12 hours. After completion of the reaction, water was added to the reaction solution, and extraction was performed 3 times with ethyl acetate. The organic layer was collected, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), thereby obtaining 0.50 g of 4-(2-phenyl-1-ethynyl)aniline (Compound 4-1).

Workup

additionwas added to the reaction solution, and extraction
customThe organic layer was collected
washwashed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-217e9ee0b9da48a883a3c66d28f8eba6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785649B2

Reaction notes

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