p-Fluoronitrobenzene → HCID 15079649, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 9.3 g (0.032 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one in approximately 30 ml of N,N-dimethylformamide was added to a stirred mixture of 1.5 g (0.030 mole) of sodium hydride (50% suspension in oil) in 100 ml of N,N-dimethylformamide. The mixture was stirred for 15 minutes and 4.50 g (0.0304 mole) of 4-fluoronitrobenzene was added. This mixture was stirred at room temperature for approximately 18 hours then was heated at 80° C. for five hours. The mixture was cooled, poured into ice water and was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a solid residue. This residue was purified by recrystallization from n-heptane to yield 8.1 g of 1-[4-chloro-2-fluoro-5-(4-nitrophenoxy)phenyl]-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one, m.p. 109°-110° C.

Provenance & Evidence