Hydrochloric Acid → 2-Iodo-4-methylphenol

Temperature

0 °C

4-Methylphenol (2.69 g, 24.86 mmol) was dissolved in 50 mL of methanol, and then sodium iodide (3.84 g, 25.60 mmol) and sodium hydroxide (1.16 g, 29.00 mmol) were added. Under nitrogen atmosphere, the solution was cooled down to 0° C. One equivalent of sodium hypochlorite (5.0% NaOCl, 40.0 mL) was added drop wise adjusting the drip rate to maintain a reaction temperature of 0-3° C. A red color appeared and faded instantly when sodium hypochlorite hit the solution. After complete addition, the mixture was stirred for 1 hr at 0-3° C. Then, 10% aqueous sodium thiosulfate solution (28.0 mL) was added and the pH was adjusted to 3-4 using 5% hydrochloric acid or until a white suspension came out. The reaction mixture was extracted with diethyl ether 3×50 mL. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the solvent was removed in vacuo to afforded light yellow oil, which solidified upon standing. The crude solid was purified by column chromatography (hexane:dichloromethane, 1:3 as the eluent) to afford a white solid (4.54 g, 77.9% yield). 1H NMR δ 2.24 (s, 3H), 5.16 (s, 1 H), 6.85 (d, J=8.3, 1H), 7.01 (dd, J=8.3, and 2.1, 1H), 7.46 (dd, J=1.5, 1H). m.p.: 34.5-35.5° C.

1. temperatureto maintain a reaction temperature of 0-3° C
2. additionAfter complete addition
3. extractionThe reaction mixture was extracted with diethyl ether 3×50 mL
4. washThe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customthe solvent was removed in vacuo
8. customto afforded light yellow oil, which
9. customThe crude solid was purified by column chromatography (hexane

ORD record

ord-62c03534d8d3445db52943dce653512f

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473786B1