Potassium Carbonate → 1-(3-Bromophenyl)-2-(diallylamino)ethanone

HRID 77563

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](=[O:14])[CH2:12]Br.[CH2:18]([NH:21][CH2:22][CH:23]=[CH2:24])[CH:19]=[CH2:20]>C(#N)C>[Br:7][C:8]1[CH:9]=[C:10]([C:11](=[O:14])[CH2:12][N:21]([CH2:22][CH:23]=[CH2:24])[CH2:18][CH:19]=[CH2:20])[CH:15]=[CH:16][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Potassium carbonate (38.8 g, 281 mmol) is added to 3-bromophenacyl bromide (60 g 216 mmol) in acetonitrile (430 mL), and the mixture is cooled under nitrogen to 0° C. Diallylamine (34.6 mL, 280.63 mmol) is added drop wise over 1 hour and the reaction is allowed to warm to 22° C. overnight. The crude reaction mixture is concentrated and the residue is partitioned in water (300 mL) and MTBE (300 mL). The aqueous layer is discarded and the organic layer is washed with water (100 mL, 2×) and with brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and the solvent evaporated to constant weight to give the title compound (62 g, 98%). ES/MS (m/e): 294 (M+1).

Aufarbeitung

temperatureto warm to 22° C. overnight
customThe crude reaction mixture
concentrationis concentrated
customthe residue is partitioned in water (300 mL)
washthe organic layer is washed with water (100 mL, 2×) and with brine (100 mL)
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
customthe solvent evaporated to constant weight

Quellen und Nachweise

ORD-Eintrag: ord-97c2129e07374dcf8c1acfa9497f141a
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841293B1

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