Water → 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine

HRID 383372

Reaktionsgleichung

[CH3:1][N:2]([CH3:6])[CH2:3][C:4]#[CH:5].BrC1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10]C=1[N+]([O-])=O.C([N:20]([CH2:23][CH3:24])CC)C.CN(C=[O:29])C.[OH2:30]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:14][C:12]1[CH:11]=[CH:10][C:24]([C:5]#[C:4][CH2:3][N:2]([CH3:6])[CH3:1])=[C:23]([N+:20]([O-:29])=[O:30])[CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a flask charged with N,N-dimethylprop-2-yn-1-amine (737 mg, 945 μL, 8.86 mmol), 2-bromo-4-fluoro-1-nitrobenzene (1300 mg, 5.91 mmol), PdCl2(PPh3)2 (415 mg, 0.59 mmol), CuI (169 mg, 0.89 mmol) were added triethylamine (2.47 mL, 17.73 mmol) and DMF (10 mL) under N2 atmosphere. The reaction mixture was heated at 60° C. for 5 h, then poured into water (300 mL) and extracted with ethyl acetate (3×40 mL). The organic fractions were combined, dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (50-100% ethyl acetate/hexanes) yielded 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine (895 mg, 68% yield). LC/MS m/z 223.0 [M+H]+.

Aufarbeitung

extractionextracted with ethyl acetate (3×40 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by silica gel chromatography (50-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-9dfeda01c4f647f5b767728a06bf0e0c
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08367660B2

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