Sulfuric Acid → 1,4-Diiodo-2-nitrobenzene

Temperature

0 °C

1,4-Diiodo-2-nitrobenzene 4-Iodo-2-nitroaniline (6.60 g, 0.025 mol) was suspended in water (19 mL) and glacial acetic acid (17.5 mL) (Sapountzis et al., 2005, which is incorporated herein by reference). The mixture was cooled to 0° C. Sulfuric acid (17.5 mL, 0.328 mol) was added cautiously. The mixture was cooled to minus 5° C., and a solution of NaNO2 (1.90 g, 0.028 mol) in water (7.5 mL) was added dropwise at a rate that the temperature would not exceed 0° C. Upon completion of the addition the mixture was stirred for 30 minutes and was added in small portions to a boiling solution of sodium iodide (22.33 g, 0.149 mol) in water (7.5 mL) (CAUTION: vigorous nitrogen evolution!). The resulting mixture was kept at 60° C. for one hour, then cooled down to room temperature, followed by addition of diethyl ether (500 mL). The ether solution was separated, washed twice with water (150 mL) and once saturated NaHCO3 (150 mL). The solution was dried over Na2SO4 and concentrated in vacuo to a solid, which was recrystallized from ethanol to yield 1,4-diiodo-2-nitrobenzene (9.30 g, 99%). 1H NMR (400 MHz, CDCl3): δ 8.15 (d, 1H, J=2.0 Hz), 7.75 (d, 1 H, J=8.3 Hz), 7.56 (dd, 1 H, J=8.3 and 2.0 Hz).

1. temperatureThe mixture was cooled to minus 5° C.
2. customexceed 0° C
3. additionUpon completion of the addition the mixture
4. waitThe resulting mixture was kept at 60° C. for one hour
5. temperaturecooled down to room temperature
6. customThe ether solution was separated
7. washwashed twice with water (150 mL) and once saturated NaHCO3 (150 mL)
8. dry with materialThe solution was dried over Na2SO4
9. concentrationconcentrated in vacuo to a solid, which
10. customwas recrystallized from ethanol

ORD record

ord-e64e664f9ab04b29b4c9d40bce8621f3

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200319B2