Reaktion #85739

Reaktionsgleichung

4-(1,1-difluoroethyl)-2-fluorobenzaldehyde

(R)-2-methylpropane-2-sulfinamide

→

(R,E)-N-(4-(1,1-difluoroethyl)-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide

Ausbeute 46.3%

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was placed in a pre-heated oil bath
2. 2
   Temperaturto cool to room temperature
3. 3
   Filtrationfiltered through a pad of celite
4. 4
   Waschenrinsed with DCE
5. 5
   EinengenThe combined filtrates were concentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate]

Vorschrift

To a mixture of 4-(1,1-difluoroethyl)-2-fluorobenzaldehyde (693 mg, from Step 4) and (R)-2-methylpropane-2-sulfinamide (513 mg, 4.24 mmol) in DCE (12.9 mL) was added copper(II) sulfate (882 mg, 5.52 mmol). The reaction mixture was placed in a pre-heated oil bath (55° C.) and heated for ˜2 d. The mixture was allowed to cool to room temperature, filtered through a pad of celite and rinsed with DCE. The combined filtrates were concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate] providing (R,E)-N-(4-(1,1-difluoroethyl)-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide (497 mg) as a yellow oil. LCMS m/z 292.1 (M+H)+, Rt 0.97 min.

Quelle