Reaktion #308891

Reaktionsgleichung

1-(3-Bromo-5-nitro-phenyl)-ethanone

(R)-(+)-tert-butanesulfinamide

→

title compound

2-Methyl-propane-2-sulfinic acid [1-(3-bromo-5-nitro-phenyl)-eth-(E)-ylidene]-amide

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 2.5 hrs
2. 2
   TemperaturThe reaction was cooled
3. 3
   Sonstigecarefully quenched by addition of ice and water
4. 4
   FiltrationThe white precipitate was filtered off
5. 5
   Extraktionthe aqueous mixture was extracted with ethyl acetate
6. 6
   WaschenThe organic phases were washed with water and brine
7. 7
   Trocknendried over Na2SO4
8. 8
   SonstigeVolatiles were removed under reduced pressure
9. 9
   SonstigeThe crude product was purified by automated column chromatography (cyclohexane/ethyl acetate)

Vorschrift

1-(3-Bromo-5-nitro-phenyl)-ethanone (11.6 g, 47.5 mmol), (R)-(+)-tert-butanesulfinamide (6.34 g, 52.3 mmol) and Ti(OEt)4 (24.64 ml, 119 mmol) were mixed in 62 ml THF and refluxed for 2.5 hrs. The reaction was cooled and carefully quenched by addition of ice and water. The white precipitate was filtered off and the aqueous mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as yellow oil. 1H-NMR (500 MHz, DMSO-d6): 8.58 (s, 1H), 8.55 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H), 1.24 (s, 9H); MS: 347 [(M+H)+]; [α]D=+54.5° (c=0.481% in chloroform).

Quelle