Potassium Iodide → 3-(Cyclopentyloxy)-4-(difluoromethoxy)benzaldehyde

Participants

Reaction Steps

A solution of 3-cyclopentyloxy-4-hydroxybenzaldehyde (5.1 g) in dimethylformamide (50 mL) is treated with potassium carbonate (4.83 g) and potassium iodide (1.2 g) and the solution is heated at 70°-75° C. whilst difiuorochloromethane is bubbled though it at a slow rate, during 5 hours. Water (100 mL) is added and the mixture is extracted with ethyl acetate (2×100 mL). The combined organic extracts are dried over magnesium sulfate and concentrated to give a brown oil. The oil is subjected to flash chromatography, eluting with a mixture of diethyl ether and pentane (1:4 v/v), to give 3-cyclopentyloxy-4-difluoromethoxybenzaldehyde, in the form of a pale yellow oil (4.7 g). [NMR (CDCl3): 9.92(s,1H);7.5-7.24(m,3H); 6.34-5.96(t,1H); 4.9(m,1H);2.0-1.6(m,8H)].

Provenance & Evidence