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

Temperature

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%). 1H NMR (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 record

ord-266a053e03574460a841a0ad7cca8813

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504427B2