5-IODO-6-NITRO-1,3-BENZODIOXOLE synthesis

Yield:7106-74-3 38%

Reaction Conditions:

Stage #1: 2-amino-4,5-methylenedioxy-1-nitrobenzenewith hydrogenchloride in water at 5; for 0.166667 h;
Stage #2: with potassium iodide in water at 5;

Steps:

62.a

A suspension of compound 6-nitrobenzo[d][1,3]dioxol-5-amine (2.65 g, 14.6 mmol) in con. HCl (15 mL) and water (5 mL) was heated on a steam bath for 5 min and then cooled to 5° C. with stirring. A solution of sodium nitrite (1.0 g, 14.4 mmol) in water (15 mL) was added until all the solids dissolved. The solution was stirred for additional 5 min and a solution of potassium iodide (2.4 g, 14.5 mmol) in water was then added rapidly with vigorous stirring at 5° C. The mixture was filtrated and the residue was dissolved with dichloromethane, dried and purified by column chromatograph (ethyl acetate/petroleum ether=1/10) to provide the title compound 0107-113 (1.6 g, 38%) as a yellow solid. 1H NMR (DMSO-d⁶) δ 6.24 (s, 2H), 7.64 (s, 1H), 7.67 (s, 1H).

References:

US2008/234314,2008,A1 Location in patent:Page/Page column 59