Potassium Iodide → 1-Fluoro-2-iodo-5-methyl-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-4-methyl-5-nitro-aniline (1.30 g, 7.64 mmol) was suspended in concentrated hydrochloric acid (4 mL) and cooled to 0° C. Solution of sodium nitrite (0.58 g, 8.40 mmol) in water (2.6 mL) was added dropwise while maintaining the temperature at 0-5° C. After stirring for 15 min, the mixture was filtered through a cotton pad and slowly poured into a solution of potassium iodide (4.44 g, 26.7 mmol) in water (16 mL). After standing overnight, the reaction mixture was diluted with EtOAc, washed with 10% aq NaOH and 5% aq Na2S2O5 successively, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (ethyl acetate:hexane; 2:98) to afford 1-iodo-2-fluoro-4-methyl-5-nitro-benzene as a colorless oil (1.60 g, 74%). 1H NMR (CDCl3, 400 MHz,): 2.61 (s, 3H), 7.05 (d, J=8.0 Hz, 1H), 8.44 (d, J=5.8 Hz, 1H). 13C NMR (CDCl3, 100 MHz,): 20.7, 119.1, 136.2, 137.3, 145.7, 163.9.

Provenance & Evidence