Potassium Hydroxide → HCID 90404004, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-5-fluoro-2-nitroaniline (8.5 g, 36 mmol) was stirred in 200 mL ethanol and treated with 45% KOH solution (4.5 g, 36 mmol) to produce a dark solution. This solution was cooled to 0-5° C. and treated dropwise with 6% NaOCl solution (84 g, 68 mmol) over 20 min while maintaining the temperature below 10° C. After 90 min, the mixture was diluted with 300 mL water and extracted twice with 200 mL portions of ethyl acetate. The combined extracts were washed with 30 mL saturated NaCl, dried (Na2SO4) and evaporated. The crude material was chromatographed on silica gel with a 0-30% ethyl acetate-hexane gradient to give the title compound as pale yellow solid (3.5 g, 42%): mp 87-89° C.; 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 7.23 (s, 1H); 19F NMR (376 MHz, CDCl3) δ −96.03; EIMS m/z 232.

Provenance & Evidence