4-Fluoro-3-nitrobenzotrifluoride → HCID 26189352, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of NaHCO3 (3.9 g, 48 mmol), 1-fluoro-2-nitro-4-trifluoromethylbenzene (4.0 g, 19 mmol), and 3-dimethylamino-1-propanol (2.5 ml, 21 mmol) in 38 mL dry THF was heated with a reflux condenser under nitrogen for 12 h. The mixture was filtered through a fritted funnel into a flask. The solution was cooled to 0° C. and was treated with potassium tert-butoxide (2.4 g, 21 mmol) resulting in an orange solution. The solution was warmed to ambient temperature and was allowed to stir for 1 h. The solvent was removed in vacuo, and the resulting brown oil was partitioned between saturated aqueous NaHCO3 and methylene chloride. The aqueous layer was extracted three times with methylene chloride. The combined organic layers were dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (MC/MeOH/conc. NH4OH) to provide the desired compound as an orange oil. MS (m/z): 293.1 (M+H)+. Calc'd for C12H15F3N2O3: 292.25.

Provenance & Evidence