| 90% |
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 24h; Ambient temperature; |
|
| 90% |
With iodine; silver nitrate In neat (no solvent, solid phase) at 20℃; for 1.03333h; Milling; |
3-Iodo-1,2,4,5-tetramethylbenzene (2)
A mixture of I2 (5.7 g, 22.6 mmol) and AgNO3 (3.8 g, 22.6 mmol) was gently blended in an agate mortar for 2 min, and then the aromatic substrate 1,2,4,5-tetramethylbenzene (3.0 g, 22.6 mmol) was added. The homogeneous mixture was additionally ground for 30 min at room temperature; the color of the mixture changes to grayish-green then to yellow and after a 2-min break, the grinding was continued for an additional 30 min. The resulting mixture was extracted with diethyl ether, and the ether extract was filtered and concentrated on a rotary evaporator. Recrystallization of the residue from PE afforded 5.3 g (90%) of 2 as a white solid. mp: 80-81 oC (lit.[2] mp: 78-79 oC) 1H NMR (CDCl3, 300 MHz) δ 6.89 (s, 1H), 2.44 (s, 6H),2.31 (s, 6H); FT-IR (KBr) 511 (νC-I) cm-1 |
| 89% |
With copper diacetate; iodine In acetic acid for 6h; Heating; |
|
| 88% |
With iodine; Selectfluor In acetonitrile at 55 - 65℃; for 1.5h; |
|
| 88% |
With Iodine monochloride at 20℃; for 1h; |
|
| 87% |
With bismuth(III) nitrate; iodine; silica gel at 20℃; for 0.0833333h; |
|
| 87% |
With iodine; silver nitrate at 20℃; |
|
| 83% |
With potassium permanganate; sulfuric acid; iodine In water; acetic acid at 100℃; for 1.5h; |
|
| 82% |
With phenyltrimethylammonium dichloroiodate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 100℃; for 4h; |
|
| 80% |
With [bis(acetoxy)iodo]benzene; iodine at 20℃; for 0.75h; |
|
| 79% |
With sulfuric acid; iodine; periodic acid In water; acetic acid at 65℃; |
|
| 76% |
With sulfuric acid; Iodine monochloride at 95 - 100℃; for 2.5h; |
|
| 74% |
With tetraiodoglycoluril; sulfuric acid In 1,4-dioxane at 20℃; for 0.25h; |
|
| 71% |
With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; sulfuric acid In ethanol at 20℃; for 0.333333h; |
|
| 65% |
With sodium nitrate; iodine; acetic acid at 116℃; for 6h; |
|
| 56% |
With ammonium cerium(IV) nitrate; tetra-(n-butyl)ammonium iodide In acetonitrile for 240h; Ambient temperature; |
|
|
With iodine durch Schmelzen; Behandeln mit Quecksilberoxyd; |
|
|
With iodine; mercury(II) oxide; Petroleum ether |
|
|
With iodosulfur; nitric acid; Petroleum ether |
|
|
With water; iodine; iodic acid; acetic acid |
|
|
With 4-iodoanisol; sulfuric acid In cyclohexane |
|
|
With iodine; silver sulfate; trifluoroacetic acid; trifluoroacetic anhydride In acetic acid; acetonitrile for 0.133333h; Ambient temperature; aromatic iodination: competition reaction with mesitylene: kMES/kDUR; other Ag salts, other times; kinetic isotpe effect: kH/kD; |
|
| 69 % Chromat. |
With air; bismuth (III) nitrate pentahydrate; iodine In acetonitrile at 20℃; for 12h; |
|
Chemistry
Pharmaceutical Intermediates
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Material Science
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