Hydrochloric Acid → 1-Trifluoromethyl2,4,6-trinitrobenzene

Participants

Reaction Steps

A mixture of potassium trifluoroacetate (210 mg, 1.4 mmol and 1,3,5-trinitrobenzene (100 mg, 0.47 mmol) in one mL of N,N-dimethylformamide (DMF) or in one mL of dimethylsulfoxide (DMSO) was heated at 150° C. for one hour. A deep red solution of a Meisenheimer complex of formula (II) above (Z=nitro; Q=trifluoromethyl; R and R'=H; M=K; and n=1) was obtained. The structure of the complex was verified by NMR spectroscopy. Oxidation of a DMF solution of this complex by dropwise addition of tert-butylhypochlorite until the red color disappeared (about seven drops) followed by aqueous workup (10 mL of 1M HCl, extracted with three portions of diethyl ether afforded an oil. This was purified by preparative thin layer chromatography (one 2 mm silica gel plate eluted with 50% petroleum ether/50% dichloromethane) to give 53 mg (40% yield) of 1-trifluoromethyl2,4,6-trinitrobenzene.

Provenance & Evidence