Reaktion #665965

Reaktionsgleichung

hydrochloric acid

4-chloro-3-nitrobenzaldehyde

benzyltriphenylphosphonium bromide

sodium hydride

→

2-chloro-5-((Z)-2-phenylvinyl)-1-nitrobenzene

Ausbeute 56.5%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with methylene chloride
2. 2
   WaschenThe extract was washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Sonstigethe solvent was removed under reduced pressure
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1)

Vorschrift

To a suspension of 4-chloro-3-nitrobenzaldehyde (1 g) and benzyltriphenylphosphonium bromide (2.34 g) in toluene (35 mL) was added sodium hydride (55%, 0.28 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with methylene chloride. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1) to give 2-chloro-5-((Z)-2-phenylvinyl)-1-nitrobenzene (0.79 g). The obtained 2-chloro-5-((Z)-2-phenyl -vinyl)-1-nitrobenzene (0.16 g) was dissolved in ethanol (6 mL) -methanol (2 mL). To the solution was added 5% rhodium-carbon powder (20 mg) and morpholine (5 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (87 mg).

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