Trimethylsilylacetylene → 3-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

HRID 931002

Reaktionsgleichung

[Br:1][C:2]1[C:3](I)=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>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.C(N(CC)CC)C>[Br:1][C:2]1[C:3]([C:15]#[C:14][Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 3-bromo-2-iodo-5-(trifluoromethyl)aniline (5.21 g), ethynyl(trimethyl)silane (2.21 mL), triethylamine (100 mL), dichlorobis(triphenylphosphine)palladium(II) (1.00 g) and copper(I) iodide (0.271 g) was stirred overnight at 80° C. under nitrogen atmosphere. The solvent was evaporated under reduced pressure, to the residue was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.70 g).

Aufarbeitung

customThe solvent was evaporated under reduced pressure, to the residue
additionwas added saturated aqueous ammonium chloride solution
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-c3d634ed7fb94bde88394e1c8c988508
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09296746B2

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