Reaktion #602264

Reaktionsgleichung

2-fluoro-4-(trifluoromethyl)benzaldehyde

4-fluorophenol

dicesium carbonate

→

2-(4-fluorophenoxy)-4-(trifluoromethyl)benzaldehyde

Ausbeute 78.5%

Lösungsmittel

ethyl acetate

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled to room temperature
2. 2
   WaschenThe organic layer was washed with water (2×10 mL)
3. 3
   Trocknendried with MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto yield a brown oil that
7. 7
   Sonstigewas purified by column chromatography

Vorschrift

To a solution of 2-fluoro-4-(trifluoromethyl)benzaldehyde (1.0 g, 5.20 mmol) and 4-fluorophenol (583.5 mg, 5.20 mmol) in DMF (5.0 mL) was added dicesium carbonate (1.7 g, 5.20 mmol) and the mixture was heated at 100° C. for 1 hour. The reaction was cooled to room temperature. The reaction was diluted with ethyl acetate (5 ml) and water (10 ml). The organic layer was washed with water (2×10 mL), dried with MgSO4, filtered and evaporated to yield a brown oil that was purified by column chromatography using a gradient of ethyl acetate in hexanes (0-25%) to yield 2-(4-fluorophenoxy)-4-(trifluoromethyl)benzaldehyde (1.16 g, 78%). 1H NMR (400 MHz, CDCl3) δ 10.58 (s, 1H), 8.04 (d, J=8.0 Hz, 1H), 7.42 (d, J=7.5 Hz, 1H), 7.18-7.04 (m, 5H) ppm.

Quelle