3-Iodophenol

yellow-beige to grey crystalline powder, crystals

3-iodophenol is an iodophenol.

To a suspension of 3-aminophenol (1kg, 9.16mol) in 10percent hydrochloric acid (600mL) was added a solution of sodium nitrite (948g, 13.75mol) in water (300mL) at 0°C dropwise and then stirred at 0°C for 30min. To the mixture was added urea (440g, 7.33mol) slowly portionwise, and then stirred at 0°C for 1h, after which in a separate flask, potassium iodide (3.04kg, 18.33mol) suspended in water (1L) and 1, 2-dichloroethane (1L) were added to the suspension. This mixture was cooled to 0°C, and then poured slowly into the diazonium mixture. The reaction was stirred for 30min at 0°C, then allowed to warm to room temperature and stirred for another 2h. The reaction mixture was filtered through Celite and the solid was rinsed with dichloromethane. The organic phase was washed with water and dried over anhydrous NaAt room temperature, a 25percent sulfuric acid solution was pumped into a Straight Static Mixer A at a rate of 50.2 g / min using an electromagnetic metering pump and the meta-iodoaniline was pumped into a straight stationary Mixer A, Straight static mixer A heat conducting oil temperature is set to 10.0 , 30percent of the sodium nitrite solution with Hanbon-NP7010C high-performance liquid pump at a rate of 6g / min pumped into the heart static mixer B, The temperature of the heat-conducting oil of the B was set to 10.0 ° C, The reaction results in a diazonium salt solution. The temperature of the HTF in the heart tube reactor was set to 88 ° C while the diazonium salt aqueous solution was pumped into the heart tube reactor at a rate of 1 ml / min using a Hanbon-NP7010C HPLC pump, After the reaction solution into the heartType oil-water separator, collecting 120min, finally get11.4 g of m-iodophenol, purity 99.1percent, yield 92.5percent.General procedure: A solution of 4-iodotoluene (1.05 g, 4.83 mmol) in a mix of 19.3 mL of n-Bu4NOH 1.5 M aqueous solution and 19.3 mL of DMSO (for an overall 0.125 M solution vs 4-iodotoluene) was prepared. Using Flow commander software, a continuous flow experiment was designed in order to control the flow stream of the pump matching 20 min of residence time (the flow stream was set at 0.50 mL/min). 37 mL of the reaction solution was injected (corresponding to 4.63 mmol of 4-iodotoluene that will be used to calculate the isolated yield; this method being used in order to maximise the reproducibility for the reported yield)using direct injection mode and the reagent stream was pumped into the 10 mL copper reactor (1.0 mm i.d.) at 150 °C. 2 X 8 bar back pressure regulators (BPR) were placed in series atthe end of the reactor, allowing safe heating of the solvent. 48 mL of the crude reaction solution was then collected into 100 mL glass vial. A reconditioning, consisting of 3 mL of DMF followed by 3 mL of a 10percent aqueous acetic acid solution, was run after the experiment in order to clean the reactor. The crude reaction solution was then acidified to pH = 1 with 2 N HCl. Water (150 mL) was added and the mixture was extracted with Et2O (3 X 150 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under vacuum. The crude mixture was purified by automated flash column chromatography using a 24 g column and a 30-80percent DCM/Hexanes gradient affording 406 mg of 2a (81percent yield).

Molecular Weight:220.01
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:219.93851
Monoisotopic Mass:219.93851
Topological Polar Surface Area:20.2
Heavy Atom Count:8
Complexity:74.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes