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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence