2-Iodobenzonitrile

Yellow solid

General procedure: To a 25 mL Schlenk tube containing a solution of 2 in 2 mL of THF was added amide (1.0 mmol) and (EtO)General procedure: To a 25ml Schlenk tube containing a solution of 1 in 2ml of THF was added amide (1.0 mmol) and (EtO)General procedure: Aniline derivative (2 mmol) was dissolved in 1 ml of 37 percent HCl. The mixture was stirred at 0–5 C for 10 min, until the ammonium salt was formed and the aromatic amine disappeared. The progress of the reaction was monitored by TLC [eluent: n-hexane/ethyl acetate (80:20)]. Nitrite ionic liquid (1 mmol) was added to the aniline solution. The reaction mixture was ground mildly for 5–10 min, the diazonium salt was formed.Then, KI (5 mmol, 0.41 g) was added to the mixture and stirring continued for 5–20 min at room temperature (Table 1). The mixture was filtered and washed with distilled water (3 x 8 ml) and ethyl acetate (EtOAc, 15 ml). The residue was extracted with EtOAc (3 9 10 ml) and the combined organic layer was washed with 10 percent aqueous solution of Na2SO3 (15 ml) and then it was dried over anhydrous Na2SO4. The solvent was evaporated to afford aryl iodides.General procedure: Potassium iodide (5.0 mmol) and sodium nitrite (3.0 mmol) was added at room temperature to a solution of aniline (2.5 mmol) and camphorsulfonic acid (3.0 mmol) in acetic acid (30 ml), and the mixture was stirred for 24 h. The evolution of NThe reaction was carried out using o-iodobenzyl alcohol (i.e., R1 in the formula (I) o) 1.0 mmol (234.0 mg)The procedure and procedure were the same as in Example 1, aqueous ammonia (1.6 mol / L) 5.0 mL, catalyst copper sulfate was used in an amount of 5 molpercent (8.0 mg)TEMPO is used in an amount of 8 molpercent (12.5 mg) at a reaction temperature of 120 ° C and a reaction time of 18 h. The crude product is purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure title product at 206.1 mg yield of 90percent.General procedure: To a solution of alcohol (1 mmol) in MeCN–H2O (9:1, 3 mL) were successively added TEMPO (7.8 mg, 5 molpercent), NH4OAc (0.308 g, 4 equiv), and PhI(OAc)2 (0.708g, 2.2 equiv). The suspension was stirred at roomtemperature (progress of the reaction was monitored byTLC) for the reaction time indicated in Table 2. The resultantclear two-phase reaction mixture was concentrated, dilutedwith H2O and Et2O, and the organic layer was dried (Na2SO4), filtered, and evaporated under reduced pressure.The residue was purified by flash column chromatography(PE–Et2O or PE–CH2Cl2) to give 2.General procedure: NaOWas added 2-iodo-benzaldehyde (1.0 mmol) in a round bottom flask, acetonitrile (2ml), trimethylsilyl azide (3.0mmol), stirred for 1-2 min at 80 deg.] C in a heating block, then added CuBrGeneral procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 μmmol, 6.7 mg), NIS (1.5mmol, 337.5 mg) and I2 (60 μmol, 20 molpercent) were added. The tube was evacuated and backfilledwith argon for three times, and then 3 mL of dry DCE was added through a syringer under argon.The tube was sealed with Parafilm Mr® and placed in an oil bath with a contact thermometer, andthe reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λmax = 455 nm).After 24 h or 36 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and thesilica was washed with DCM) (50 mL). The filtrate was collected and the solvent was removed invacuo. The crude residue was purified by silica gel flash column chromatography to provide thetarget product (2). (Note: The reaction was very sensitive to moisture, and the yields sharplydecreased to less than 5percent when 0.01 equivalent of H2O was added to the reaction system).

suzuki reaction

Molecular Weight:229.02
XLogP3:2.5
Hydrogen Bond Acceptor Count:1
Exact Mass:228.93885
Monoisotopic Mass:228.93885
Topological Polar Surface Area:23.8
Heavy Atom Count:9
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes