Water → 2-Iodo-6-nitrobenzonitrile

Participants

Reaction Conditions

Reaction Steps

2-Amino-6-nitrobenzonitrile (Example 130e) (4.32 g, 26.5 mmol) was added in small portions to a suspension of sodium nitrite (2.19 g, 31.7 mmol) in concentrated H2SO4 (43 mL) and acetic acid (43 mL) at 45° C. The reaction was heated at 45° C. for 1 h and then added in small portions to a solution of potassium iodide (7.47 g, 45.0 mmol) in H2SO4 (1 M, 43 mL). After stirring at room temperature for 1.5 h, iced water was added to the reaction and the precipitated product was collected by filtration. The product was purified by chromatography on silica gel eluting with CH2Cl2, to give 2-iodo-6-nitrobenzonitrile (3.86 g, 53%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.46-8.52 (m, 1H), 8.34-8.38 (m, 1H), 7.66-7.71 (m, 1H).

Provenance & Evidence