Month: August 2021

Synthetic Route of 618-91-7, The chemical industry reduces the impact on the environment during synthesis 618-91-7, name is Methyl 3-iodobenzoate, I believe this compound will play a more active role in future production and life.

Intermediate 73a: Methyl 3-(3-hydroxyprop-1-yn-1-yl)benzoate Bis(triphenylphosphine)palladium(II) dichloride (0.67 g, 0.95 mmol) was added in one portion to methyl 3-iodobenzoate (5 g, 19.08 mmol) and copper(I) iodide (0.18 g, 0.95 mmol) in degassed THF (90 mL) at 20 C. under nitrogen. The resulting mixture was stirred for 5 minutes then prop-2-yn-1-ol (2.22 mL, 38.16 mmol) and triethylamine (5.31 mL, 38.16 mmol) was added. The reaction was stirred at 20 C. for 18 hours. The reaction mixture was diluted with EtOAc (200 mL), and washed sequentially with water (2*100 mL) and saturated brine (50 mL). The organic layer was dried with MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane to afford the title compound (3.10 g, 85%) as a yellow solid; 1H NMR (400 MHz, CDCl3, 30 C.) 1.69 (1H, t), 3.92 (3H, s), 4.51 (2H, d), 7.40 (1H, t), 7.61 (1H, dt), 7.99 (1H, dt), 8.11 (1H, d).

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, Methyl 3-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; YANG, Bin; KETTLE, Jason Grant; HAYHOW, Thomas George Christopher; RASMUSSON, Timothy Gordon; NISSINK, Johannes Wilhelmus Maria; FALLAN, Charlene; Lamont, Gillian McGregor; (308 pag.)US2019/194190; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 249647-24-3, name is Methyl 3-bromo-4-iodobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H6BrIO2

A solution of methyl 3-bromo-4-iodobenzoate (Preparation 23, 4.3 g, 12.6 mmol) in CH2Cl2 was cooled, under N2, to -78 C. DIBAL-H was added slowly to the solution, which was stirred at -78 C. for 45 minutes and then allowed to come to room temperature. Next, the reaction mixture was diluted with 1M HCL (40 mL) and stirred for 30 minutes. The reaction was further diluted with water and extracted with CH2Cl2. The organic phase was dried (Na2SO4) and concentrated under vacuum to afford the intermediate (3.2 g, 82%) as a solid. 1HNMR (CDCl3): 7.85 (1H), 7.67 (1H), 7.02 (1H), 4.65 (2H), 1.76 (1H, OH).

The synthetic route of 249647-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vaillancourt, Valerie A.; Chubb, Nathan Anthony Logan; Curtis, Michael; Howson, William; Kyne, Graham M.; Menon, Sanjay; Sheehan, Susan M. K.; Skalitzky, Donald J.; Wendt, John A.; US2012/35122; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 2142-70-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2142-70-3, name is 1-(2-Iodophenyl)ethanone belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 10mL-sealed tube was charged with aryl iodides or bromides (1mmol), CuI (19mg, 0.1mmol), and DMEDA (13mg/16muL, 0.15mmol) in NH4OH (1.5mL, 27% NH3 in H2O) and DMSO (0.5mL). The tube was flushed with Ar gas before being capped. The solution was stirred for the given times at 130C or 110C. The resulting suspension was cooled to room temperature and saturated aqueous Na2SO4 solution (5mL) was added. The resulting solution was extracted with EtOAc (20mL×3). The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (hexanes/EtOAc=5/1?1/2 or EtOAc) to give the desired primary arylamines.

The synthetic route of 1-(2-Iodophenyl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jung, Hee Seon; Yun, Taeil; Cho, Yungyeong; Jeon, Heung Bae; Tetrahedron; vol. 72; 40; (2016); p. 5988 – 5993;,
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 199850-56-1 as follows. Product Details of 199850-56-1

General procedure: To a solution of methyl 2-amino-4-chlorobenzoate (300 mg, 1.6 mmol) and ethyl 2-phenoxyacetate (320 mg, 1.8 mmol) in anhydrous THF (9 mL) was added KHMDS (4.8 mL, 1.0 M in THF, 4.8 mmol) in one portion with vigorous stirring under a nitrogen atmosphere. The reaction mixture was stirred at rt until completion of the reaction (10 min) then MeOH was added. The reaction mixture was concentrated under reduced pressure and the resulting residue was taken up in water and acidified with 1 N HCl until precipitation occurred. The precipitate was filtered, washed with EtOH then dried to give 7-chloro-4-hydroxy-3-phenoxyquinolin-2(1H)-one (Table 2, entry 1) as a pale pink powder (449 mg, 92%).

According to the analysis of related databases, 199850-56-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Toum, Jerome; Moquette, Alexandre; Lamotte, Yann; Mirguet, Olivier; Tetrahedron Letters; vol. 53; 15; (2012); p. 1920 – 1923;,
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 25252-00-0 as follows. Recommanded Product: 25252-00-0

Tetrahydrofuran (99.7g) and sodium borohydride (15.2g, 0.4mol) were added to the reaction flask at 10-25C.A solution of 2-bromo-5-iodobenzoic acid (109.4 g, 0.34 mol, prepared in Example 2) in tetrahydrofuran (151 g) was slowly added dropwise.At 10-30C, a solution of sulfuric acid (16.4 g) in tetrahydrofuran (25 g) was added dropwise to the reaction vessel. After the addition was completed, the reaction was performed at room temperature for 2 hours. Then, it was heated to reflux 66C, refluxed for 2 hours, and then lowered to room temperature. 5% hydrochloric acid (235 g) was slowly added dropwise and THF was distilled off under reduced pressure (-0.01 MPa).Add 326.7 g of MTBE and 222.7 g of water to dissolve the solid, cool to 15-25C, separate the layers, and evaporate the organic layer under reduced pressure (-0.095 MPa).Toluene (108.8 g) and water (108.8 g) were added and the mixture was warmed to 60C for 1 h, reduced to 18-22C and filtered. After drying, 89.1 g of an off-white solid product was obtained with a measured content of >99% and a yield of 85.1%.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jinkai (Liaoning) Chemical Co., Ltd.; Wang Yongcan; Zhang Hong; Li Zhenwei; Zhao Yang; Zhang Guifang; Song Tongji; Hu Zhenzhu; Huang Fengting; (8 pag.)CN107954861; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 39998-81-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 1-(2-fluoro-4-iodobenzyl)-4-ethyl-2-propyl-1H-imidazole-5-carboxaldehyde A solution of 2-fluoro-4-iodotoluene (47.28 g, 0.20 mol), N-bromosuccinamide (37.64 g, 0.21 mol) and azobisisobutyronitrile (3.65 g, 0.02 mol) in CCl4 (200 mL) was refluxed under N2 overnight. The mixture was cooled, the solid was filtered off and washed with CCl4. The filtrate was concentrated. The precipitated formed was filtered and washed with hexane to give 13.92 g of 86% pure benzyl bromide. The mother liquid was concentrated to give 48.88 g of 60% pure benzyl bromide. Both fractions were used without further purification in the next step. 4-Ethyl-2-propyl-1H-imidazole-5-carboxaldehyde (6.32 g, 38.0 mmol), potassium carbonate (10.57 g, 76.5 mmol), and 2-fluoro-4-iodobenzyl bromide (13.90 g of 86%, 38.0 mmol) were added together with 50 mL of DMF. The reaction mixture was stirred at room temperature overnight under N2. The solvent was removed in vacuo and the residue was partitioned between EtOAc and H2 O. The two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic mixture was washed with H2 O and brine, dried over MgSO4 and concentrated. The crude product mixture was purified by flash chromatography (silica gel, 30-50% EtOAc/hexane) to yield 10.63 g orange oil (70%). MS m/e 401.0, [M+H]+; 1 H NMR (300 MHz, CDCl3): delta0.95 (t, 3H, CH3), 1.32 (t, 3H, CH3), 1.70 (m, 2H, CH2), 2.60 (m, 2H, CH2), 2.82 (q, 2H, CH2), 5.52 (s, 2H, CH2 Ar), 6.42 (t, 1H, ArH), 7.38 (d, 1H, ArH), 7.42 (d, 1H, ArH), 9.73 (s, 1H, CHO).

The synthetic route of 2-Fluoro-4-iodo-1-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Du Pont Merck Pharmaceutical Company; US5395844; (1995); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 103962-05-6, The chemical industry reduces the impact on the environment during synthesis 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

To a solution of compound 03-4-1 (5.30 g, 20.6 mmol, 1.0 eq) in toluene (150 mL) was added 1-iodo-4-(trifluoromethoxy)benzene (7.12 g, 24.7 mmol, 3.87 mL, 1.2 eq), K3PO4 (10.9 g, 51.5 mmol, 2.5 eq), (1S,2S)-N1,N2-dimethylcyclohexane-1,2-diamine (879.0 mg, 6.18 mmol, 0.3 eq) and CuI (392.3 mg, 2.06 mmol, 0.1 eq) under N2 protection. The mixture was stirred at 110 °C for 18 h, cooled to room temperature, quenched by addition of H2O (250 mL) at room temperature, and diluted with EtOAc (250 mL). The organic layer was separated, washed with brine (300 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2) to give compound 03-4-2 (7.00 g, 81percent yield).

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-4-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYRAS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; (587 pag.)WO2017/96045; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, 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 2265-91-0, name: 1,3-Difluoro-5-iodobenzene

In a nitrogen atmosphere, carbazole and potassium tert-butoxide powder were dissolved in 20 mL of anhydrous dimethyl sulfoxide solution, and after mixing well, the reaction temperature rose to 120 C. After the temperature was stabilized, The solution of 1-iodo-3,5-difluorobenzenein anhydrous dimethyl sulfoxide was heated to 140 C after the dropwise addition, and the reaction time was 2 hours. Among them, 1-iodo-3,5-difluorobenzene, carbazole, and tert-butanol The molar ratio of potassium is 1: 2.1: 2.1; the mixed solution is cooled to room temperature and extracted, dried, and rotary solvent is used to remove excess solvent to obtain a crude product. The crude product was separated and purified by column chromatography to obtain compound DCzB-I. The eluent was chloroform: n-hexane = 1: 10 (volume ratio), and the yield was 75%.

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, 1,3-Difluoro-5-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fuzhou University; Guo Zhiyong; Xiao Hui; Lou Yuheng; Han Mingxi; (11 pag.)CN110272379; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, molecular formula is C8H7IO2, 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. HPLC of Formula: C8H7IO2

General procedure: A mixture of 2-iodo-5-methylbenzoic acid (2a; 0.2 mmol, 1equiv), styrene 1a (0.8 mmol, 4 equiv) and NaHCO3 (0.26 mmol,1.3 equiv) in DMSO (4 mL) was put into a quartz reaction tube(10 mL). N2 was flowed in for 10 min, then the tube was sealed and exposed to illumination with a high-pressure mercury lamp at 300 nm wavelength for 6 h. Water (20 mL) was added tothe reaction system and the mixture was extracted with ethyl acetate (3 × 20 mL). The organic phase was washed with saturated salt water, dried with anhydrous sodium sulfate, and thecrude products were obtained under reduced pressure and concentration.The purified products were purified by silica gel column chromatography (PE/EtOAc, 10:1), and the product 7-methyl-3-phenylisochroman-1-one 3a (75%) was obtained as apale-yellow liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108078-14-4, its application will become more common.

Reference:
Article; Zhang, Xiao; Huang, Binbin; Yang, Chao; Xia, Wujiong; Synlett; vol. 29; 1; (2018); p. 131 – 135;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 364-77-2, name is 2-Iodo-5-fluoronitrobenzene, 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 364-77-2, Product Details of 364-77-2

Step 1. Methyl trans-(4-Fluoro-2-nitro)cinnamate The title compound was prepared according to the procedure described in step 1 of Example 133 from 3-fluoro-6-iodonitrobenzene and methyl acrylate. 1H-NMR (CDCl3) delta: 8.67 (1H, d, 15.8 Hz), 7.78 (1H, dd, 8.07 Hz, 2.65 Hz), 7.68-7.63 (2H, m), 6.34 (1H, d, 15.8 Hz), 3.84 (3H, s).

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; Nakao, Kazunari; Stevens, Rodney William; Kawamura, Kiyoshi; Uchida, Chikara; Koike, Hiroki; Caron, Stephane; US6608070; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com