Nitric Acid → N-[4-Bromo-2-nitro-5-(trifluoromethyl)phenyl]acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of the acetamide from step (a) above (8.46 g, 30 mmol) in concentrated sulfuric acid (32.5 mL) was added dropwise concentrated HNO3 (4.1 mL, 90%. J. T. Baker) with stirring at 0° C. The resulting solution was stirred at room temperature for 3 h and poured into crushed ice (80 mL). The mixture was carefully neutralized with solid NaHCO3 and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (25% EtOAc/hexane) to give the title compound as a yellow solid. MS (ESI, neg. ion) m/z: 325.0 (M−1).

Provenance & Evidence