2-Fluoro-4-(trifluoromethyl)benzaldehyde → (NE,R)-N-[[2-fluoro-4-(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 57423

Reaktionsgleichung

[F:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>S([O-])([O-])(=O)=O.[Cu+2].ClCCCl>[F:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1/[CH:4]=[N:20]/[S@@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19]

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

To a oven dried round bottom flask with stir bar was added 2-fluoro-4-(trifluoromethyl)benzaldehyde (5 g, 26.0 mmol), (R)-2-methylpropane-2-sulfinamide (3.47 g, 28.6 mmol) and DCE (52 mL). To this mixture was then added copper (II) sulfate (6.23 g, 39.0 mmol). The reaction mixture was heated in a preheated oil bath at 55° C. for 18 hours. The reaction mixture was filtered through a pad celite, washing the solids with DCE. The filtrate was concentrated to afford a viscous green oil of (R,E)-N-(2-fluoro-4-(trifluoromethyl)benzylidene)-2-methyl propane-2-sulfinamide (7.3 g, 24.7 mmol, 95% yield). Material was taken onto next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (s, 9H) 7.44 (d, J=10.08 Hz, 1H) 7.51 (d, J=8.27 Hz, 1H) 8.13 (t, J=7.46 Hz, 1H) 8.92 (s, 1H). LCMS m/z 296.0 (M+H)+, Rt 1.02 min.

Aufarbeitung

customTo a oven dried round bottom flask
filtrationThe reaction mixture was filtered through a pad celite
washwashing the solids with DCE
concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag: ord-59cb2e214ed8410eb0426c4a8765abe5
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09434719B2

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