4-Nitrophenol → 2-Chloro-4-(4-nitrophenyloxy)-5-trifluoromethylpyrimidine

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Reaction Conditions

Reaction Steps

Yet alternatively, 0.67 g 4-nitrophenol are dissolved in 5 mL ethanol. 4.6 mL of 1 M aqueous sodium hydroxide solution are added. The mixture is cooled to −15° C. A solution of 1.0 g 2,4-dichloro-5-trifluoromethylpyrimidine in 2 mL ethanol is added at −15° C. in portions. The suspension is stirred for 1.5 hours at −15° C. to −10° C. and then warmed up to 20° C. during 3 hours. The suspension is stirred 16 hours at 20° C. The precipitate is filtered and washed with a 1:1-mixture of methanol and purified water. The product is dried in a vacuum drying oven. 1.3 g (88% of theory) of title product is obtained with a regioisomeric purity of 88:12 (2-chloro-4-(4-nitrophenyloxy)-5-trifluoromethylpyrimidine:2-(4-nitrophenyloxy)-4-chloro-5-trifluoromethylpyrimidine).

Provenance & Evidence