Reaktion #156510

Reaktionsgleichung

2,5-difluorobenzaldehyde

nitroethane

cyclohexylamine

→

1-(2,5-Difluorophenyl)-2-nitropropene

Ausbeute 81.3%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to rt the solvent
2. 2
   Sonstigewas evaporated
3. 3
   Sonstigethe residue was purified by column chromatography (silica-gel, CH2Cl2/acetone=19/1 v/v)
4. 4
   Sonstigeto give a yellow solid product, 28.5 g, 81.3% yield

Vorschrift

A mixture of 2,5-difluorobenzaldehyde (25.0 g, 0.176 mol), nitroethane (26.41 g, 0.352 mol) and cyclohexylamine (17.45 g, 0.176 mol) in 150 mL of acetic acid was stirred at 80° C. overnight. After cooling to rt the solvent was evaporated, the residue was purified by column chromatography (silica-gel, CH2Cl2/acetone=19/1 v/v) to give a yellow solid product, 28.5 g, 81.3% yield. MS: 197.6 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 7.94 (s, 1H), 7.46-7.43 (m, 1H), 7.41-7.35 (m, 2H), 2.31 (s, 3H).

Quelle