Category: 5458-84-4

Reference of 5458-84-4, A common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, molecular formula is C7H6INO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 18; N-{4-[8-(2,4-Dioxo-tetrahydro-pyrimidin-1-yl)-5-methoxy-6-trifluoromethyl-quinolin-3-yl]-phenyl}-methanesulfonamide (I-29); step 1-; A mixture of Cu(I) (10.03 g) and CsF (21.40 g) was finely ground in a mortar while in a glove bag under nitrogen atmosphere to afford a free-flowing powder and transferred to an oven dried 250 mL round bottom flask fitted with a stir bar and septum. The flask was then charged with 2-iodo-5-nitroanisole (15.17 g) and sulfolane (30 mL) and stirred rapidly at 45 C. To the mixture was added dropwise over 4 h using a syringe pump trimethyl(trifluoromethyl)silane (20 mL) and the resulting mixture stirred at RT overnight. The reaction was diluted with EtOAc (500 mL) and stirred in some CELITE 512. The reaction mixture was filtered though a pad of CELITE. The filtrate was diluted to 1 L with EtOAc and washed with 1 L of 10% aqueous NH4OH, 1 L of 1.0M HCl and 500 mL of brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The amber residue was diluted with DCM and purified by flash chromatography (770 g Supelco VersaPak SiO2 column) and eluted with a DCM/hexane gradient (0 to 40% DCM) in 10 column volumes to afford 8.61 g of 82b as a yellow crystalline solid.

The synthetic route of 5458-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; de Vicente Fidalgo, Javier; Li, Jim; Schoenfeld, Ryan Craig; Talamas, Francisco Xavier; Taygerly, Joshua Paul Gergely; US2010/311760; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5458-84-4 as follows. HPLC of Formula: C7H6INO3

Step 1 2-Methoxy-4-nitro-1-trifluoromethyl-benzene Following the procedure reported in JACS 2003, 125, 12502, 2-iodo-5-nitroanisole (2.79 g, 10.0 mmol), copper(I) iodide (2.2 eq, 4.19 g), and potassium fluoride (2.2 eq, 1.28 g) were dissolved in DMF. ClF2CCO2CH3 (4.4 eq, 4.7 ml) was added and the mixture was heated to 120 C. overnight. Upon cooling, the mixture was diluted with water and diethyl ether and filtered through celite. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate) to give 2-methoxy-4-nitro-1-trifluoromethyl-benzene (1.13 g, 51.1%) as a yellow oil.

According to the analysis of related databases, 5458-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Caroon, Joan Marie; Lopez-Tapia, Francisco Javier; US2010/160388; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5458-84-4, Recommanded Product: 5458-84-4

A mixture of 1-iodo-2-methoxy-4-nitrobenzene (1.9 g, 6.8 mmol), NaSMe (500 mg, 7.1 mmol), Pd2(dba)3 (156 mg), Xantphos (197 mg) and TEA (1.18 mL, 8.51 mmol) in THF (20 mL) was purged with argon and heated to reflux overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column (petroleum ether/ethyl acetate, 2:1, v/v) to give (2-methoxy-4- nitrophenyl)(methyl)sulfane as a yellow solid (400 mg, 30%).?H NMR (400 MHz, CDC13): 7.89 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 7.66 (d, J = 2.4 Hz, 1H), 7.15 (d, J= 8.8 Hz, 1H), 4.00 (s, 3H), 2.51 (s, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Iodo-2-methoxy-4-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVOGEN LIMITED; EIFFE, Eleanor; HEATON, Andrew; GUNNING, Peter; TREUTLEIN, Herbert; ZENG, Jun; JAMES, Ian; DIXON, Ian; (172 pag.)WO2016/187667; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 5458-84-4, A common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, molecular formula is C7H6INO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of CuCN (322 mg, 3.6 mmol) and L-proline (415 mg, 3 mmol), in DMF (15 mL) under argon, 1-iodo-2-methoxy-4-nitrobenzene (837 mg, 3 mmol) was added at room temperature. The mixture was stirred at 80 C for 45 hours. The resulting suspension was cooled to room temperature, diluted with ethyl acetate (15 mL), and washed with water. The organic phase was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica with ethyl acetate-hexane to yield 2-methoxy-4-nitrobenzonitrile (463 mg, 87%).

The synthetic route of 5458-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVOGEN LIMITED; EIFFE, Eleanor; HEATON, Andrew; GUNNING, Peter; TREUTLEIN, Herbert; ZENG, Jun; JAMES, Ian; DIXON, Ian; (172 pag.)WO2016/187667; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5458-84-4, Quality Control of 1-Iodo-2-methoxy-4-nitrobenzene

A mixture of Cu l (6.80 g, 35.84 mmol ), CsF ( 14. 15 g, 93.18 mmol ) l -iodo-2-methoxy- 4-nitrobenzene ( 10 g, 35.84 mmol ) and sulfolane (20 ml ), was stirred rapidly at 45 C. To this mixture was added trimethyl(trifluoromethyl)silane ( 13.25 g, 93. 1 mmol ) dropwise over 4 hours using a syringe pump, and the resulting mixture was stirred at 45C for 1 8 hours. The mixture was diluted with ethyl acetate (500 mL ) and stirred with Celite for 5 min. The reaction mixture was filtered through a pad of Celite, diluted with ethyl acetate ( 500 mL ). The organic layer was washed with 10% NH4OH, 1.0 N HCl, brine, dried over Na2SC>4, filtered, and concentrated to give the crude product.The crude product was purified by chromatography (ethyl acetate/petroleum ether 0/1 to 1/4) to give intermediate 444 (8 g, 91% yield ) as a white solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Iodo-2-methoxy-4-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5458-84-4, Product Details of 5458-84-4

3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridin-2-amine (20 g, 91 mmol)1-iodo-2-methoxy-4-nitrobenzene (23 g, 83 mmol)Pd (PPh 3) 4 (1 g, 0.83 mmol) and sodium carbonate (26 g, 248 mmol) were added to DME (300 mL) and water (200 mL)After sufficiently degassing the reaction mixture,And the mixture was heated under reflux for 16 hours.The reaction was cooled to room temperature,It was partitioned between EtOAc and water.The layers were separated,The aqueous layer was extracted twice with EtOAc.The combined organic layers were dried over sodium sulfate,Filtered,It was rotary evaporated.The crude material was washed with EtOAc,5.0 g of product was obtained.The filtrate was chromatographed on silica gel (1/1 hexane / EtOAc to EtOAc)A further 4.4 g of product was obtained.The total yield of 3- (2-methoxy-4-nitrophenyl) pyridin-2-amine was 9.4 g (46%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; XIA, CHUANJUN; LIN, CHUN; KOTTAS, GREGG; ELSHENAWY, ZEINAB; (78 pag.)JP6216571; (2017); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 5458-84-4, These common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 1-iodo-2-methoxy-4-nitrobenzene (2.0 g, 7.16 mmol), methyl acrylate (2.0 mL, 22.2 mmol), Pd(OAc)2 (100 mg) and PPh3 (200 mg) in DMF (20 mL) was purged with argon and heated to 70 C overnight. TLC showed that the starting material was consumed completely and a new spot had formed. The reaction mixture was diluted with ethyl acetate and the catalyst was removed by filtration. The organic layer was washed with brine, dried over Na2504 and concentrated under reduced pressure. The residue was purified by silica gel column (petroleum ether 100%) to give methyl (E)-3-(2-methoxy-4-nitrophenyl)acrylate as a yellow solid (500 mg, 31%).?H NMR (400 MHz, CDC13): 7.96 (d, J = 16.0 Hz, 1H), 7.84 (dd, J = 8.4 Hz, 2.0 Hz, 1H), 7.77 (d, J = 2.0 Hz, 1H), 7.63 (d, J = 8.4 Hz, 1H), 6.63 (d, J = 16.4 Hz,1H), 4.00 (s, 3H), 3.83 (s, 3H).

The synthetic route of 5458-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVOGEN LIMITED; EIFFE, Eleanor; HEATON, Andrew; GUNNING, Peter; TREUTLEIN, Herbert; ZENG, Jun; JAMES, Ian; DIXON, Ian; (172 pag.)WO2016/187667; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 1-Iodo-2-methoxy-4-nitrobenzene

Step 1 2-Methoxy-1-methylsulfanyl-4-nitro-benzene 2-Iodo-5-nitroanisole (5.58 g, 20.0 mmol), Pd2(dba)3 (0.025 eq, 457 mg), Xantphos (0.05 eq, 578 mg), Hunigs Base (1 eq, 3.48 ml) and sodium methanethiolate (1 eq, 1.40 g) were dissolved in THF. The mixture was heated to reflux overnight. Upon cooling the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (4:1 Hexanes/Ethyl Acetate) to give 2-methoxy-1-methylsulfanyl-4-nitro-benzene (2.72 g, 68.3%) as a yellow crystalline solid.

The synthetic route of 5458-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Caroon, Joan Marie; Lopez-Tapia, Francisco Javier; US2010/160388; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C7H6INO3

2.00 g (7.17 mmol) of 2-iodo-5-nitroanisole, 2.02 g (14.3 mmol) of (2-fluoropyridin-3-yl)boronic acid (A. Bouillon, J.-C. Lancelot, V. Collot, P. R. Bovy, S. Rault, Tetrahedron 2002, 58, 3323-3328.), 1.81 g (21.5 mmol) of sodium hydrogen carbonate and 117 mg (0.14 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride are heated to 100 C. in a degassed mixture of 40 ml of dioxane and 10 ml of water for 1 h. After cooling, the mixture is diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, clarified over activated carbon and concentrated. Purification is effected by chromatography on silica gel (eluent: dichloromethane) to obtain 1.55 g (87% of theory) of the desired product. 1H NMR (400 MHz, DMSO-d6, delta/ppm): 3.32 (d, 1H), 8.02 (ddd, 1H), 7.95 (dd, 1H), 7.92 (d, 1H), 7.64 (d, 1H), 7.49 (ddd, 1H), 4.10 (s, 3H). HPLC (Method 6): Rt=3.61 min. MS (ESIpos, m/z): 249 (M+H)+.

The synthetic route of 1-Iodo-2-methoxy-4-nitrobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA ATIENGESELLSCHAFT; US2010/298293; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com