Hydrochloric Acid → 1-Iodo-3-methoxy-5-nitrobenzene

Temperature

0 °C

To a solution of 3-methoxy-5-nitro-phenylamine (7.5 g, 44.6 mmol) in water (20 mL) was added a concentrated hydrochloric acid (19.95 mL, 267.6 mmol, 36%) at 0° C. To this was added a chilled solution of sodium nitrite (5.62 g, 80.28 mmol) in water (28.4 mL) dropwise with a vigorous stirring. Then, the resulting colored mixture was stirred for 15 min at 0° C., and a cold solution of potassium iodide (14.81 g, 89.2 mmol) in water (28.4 mL) was added carefully. During this addition, a black brown solid was formed and after addition the ice-cold bath was removed, and the reaction mixture was heated to reflux. When the production of purple vapor ceased, the mixture was cooled to room temperature and the organic compound was extracted into dichloromethane (3×200 mL). The combined organic extracts were washed with brine solution (300 mL) and dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Then, the crude residue was purified by using a LC 120 column, eluting with 0-10% ethyl acetate in hexanes to obtain 1-iodo-3-methoxy-5-nitro-benzene (10 g, 80%) as a white solid: EI(+)-HRMS m/e calculated for C7H6INO3 (M+)+ 278.9392, found 278.9393.

1. additionDuring this addition
2. customa black brown solid was formed
3. customwas removed
4. temperaturethe reaction mixture was heated to reflux
5. temperaturethe mixture was cooled to room temperature
6. extractionthe organic compound was extracted into dichloromethane (3×200 mL)
7. washThe combined organic extracts were washed with brine solution (300 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThen, the crude residue was purified
12. washeluting with 0-10% ethyl acetate in hexanes

ORD record

ord-471d599c0f134b40aba3713850a5dcd4

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093385B2