Potassium Carbonate → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde

Temperatur

65 °C

To a mixture of 4-difluoromethoxy-3-hydroxy-benzaldehyde (5.0 g, 27 mmol) and potassium carbonate (5.5 g, 40 mmol) in dimethylformamide (30 ml) under inert atmosphere at 60° C. was added bromoethylcyclopropane (5 g, 37 mmol). The mixture was stirred and heated at 65° C. After 1.5 hour, the mixture was allowed to cool and was filtered. The filtrate was concentrated under reduced pressure. The mixture was extracted with ethyl acetate (2×25 ml) and water (25 ml). The organic layer was washed with water (25 ml), brine (25 ml) and dried over magnesium sulfate. The solvent was removed in vacuo to give 3-cyclopropylmethoxy-4-difluoromethoxy-benzaldehyde as an oil (6.4 g, 100%). 1HNMR (CDCl3): δ 0.38–0.44 (m, 2H), 0.62–0.75 (m, 2H), 1.15–1.36 (m, 1H), 3.98 (d, J=4.5 Hz, 2H), 6.78 (t, JH-F=75 Hz, 1H), 7.30–7.50 (m, 3H), 9.96 (s, 1H).

1. temperatureto cool
2. filtrationwas filtered
3. concentrationThe filtrate was concentrated under reduced pressure
4. extractionThe mixture was extracted with ethyl acetate (2×25 ml) and water (25 ml)
5. washThe organic layer was washed with water (25 ml), brine (25 ml)
6. dry with materialdried over magnesium sulfate
7. customThe solvent was removed in vacuo

ORD-Eintrag

ord-534f66fb26db48c4a361a9d6265b6f90

Quelldatensatz

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07173058B2