Nitric Acid → 1,2-Dimethoxy-4-iodo-5-nitrobenzene

Temperature

100 °C

4,5-Diiodo-1,2-dimethoxybenzene (8.8 g, 23 mmol) was added into acetic acid (300 mL), and the mixture was heated to 100° C. to dissolve the solid. The clear mixture was then cooled to room temperature followed by dropwise addition of nitric acid (68-70%, 120 mL). The reaction mixture was stirred at room temperature overnight and then poured into ice-water (200 mL). The mixture was extracted by CH2Cl2 (100 mL) three times. The combined organic phase was washed with saturated NaHCO3 solution (200 mL), brine (100 mL), and dried over Na2SO4, concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield 4-iodo-5-nitro-1,2-dimethoxybenzene (5.25 g, 75%). 1H NMR (400 MHz, CDCl3): δ 7.60 (s, 1H, Ph-H), 7.38 (s, 1H, Ph-H), 3.98 (s, 3H, OCH3), 3.92 (s, 3H, OCH3).

1. dissolutionto dissolve the solid
2. temperatureThe clear mixture was then cooled to room temperature
3. extractionThe mixture was extracted by CH2Cl2 (100 mL) three times
4. washThe combined organic phase was washed with saturated NaHCO3 solution (200 mL), brine (100 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customthe residue was purified by silica gel column chromatography

ORD record

ord-8beb0a730ed74133afebe0328c6eb19f

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399798B2