Month: November 2020

These common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, 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. 624-76-0

General procedure: To a stirred solution of compound 42 (1.0 eq) and the corresponding alkyl iodide (1.0 eq) in THF (0.1 M) was added Et3N (2.0 eq) and themixture was stirred at room temperature for 20 h. The reaction mixture was purified by preparative HPLC (direct injection of reaction mixture) and the combined HPLC fractions were concentrated. The residue was dissolved in DCM and then washed with 2M aqueous NaOH, brine, dried over anhydrous Na2SO4 and then concentrated to give the product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 624-76-0.

Reference:
Article; Arns, Steve; Balgi, Aruna D.; Shimizu, Yoko; Pfeifer, Tom A.; Kumar, Nag; Shidmoossavee, Fahimeh S.; Sun, Sharon; Tai, Sheldon S.-H.; Agafitei, Olga; Jaquith, James B.; Bourque, Elyse; Niikura, Masahiro; Roberge, Michel; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 64 – 73;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 3058-39-7, name is 4-Iodobenzonitrile, molecular formula is C7H4IN, 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. 3058-39-7

To phenol (1.23 g, 13.10 mmol), copper(I) iodide (333 mg, 1.75 mmol), cesium carbonate (5.69 g, 17.47 mmol), 4-iodobenzonitrile (2.00 g, 8.73 mmol) and N,N-dimethylglycine hydrochloride (366 mg, 2.62 mmol) under nitrogen was added degassed 1,4-dioxane (10.0 mL). The whole mixture was heated at 90 C. for 88 hours. The cooled mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2¡Á100 mL). The organic layers were combined and washed with brine (100 mL) and dried with Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography EtOAc/Hex (1:12?1:8) to give the pure product as a white solid (quantitative yield). 1H NMR (300 MHz, CDCL3) delta(ppm): 7.00 (2H, d, J=9.1 Hz), 7.06 (2H, d, J=7.6 Hz), 7.23 (1H, t, J=7.2Hz), 7.41 (2H, t, J=8.1 Hz), 7.59 (2H, d, J=9.1 Hz). 13C NMR (75 MHz, CDCL3) delta(ppm): 105.9, 118.0 (CH), 119.0, 120.5 (CH), 125.3 (CH), 130.4 (CH), 134.2 (CH), 154.9, 161.8. MS (FAB+): 196 (MH+). HRMS for C13H9NO (MH+): calculated: 196.0762; found 196.0780.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3058-39-7, its application will become more common.

Reference:
Patent; UNIVERSITY OF NOTRE DAME DU LAC; US2010/261673; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-76-0, The chemical industry reduces the impact on the environment during synthesis 624-76-0, name is 2-Iodoethanol, I believe this compound will play a more active role in future production and life.

Compound 5 (1.41 g, 0.0043 mol) and potassium carbonate (1.78 g, 0.0129 mol) were added into a round bottom flask. The flask was made free of water and oxygen. The mixture was dissolved with DMF (60 ml). Then 2-iodo-ethanol (0.67 ml, 0.0086 mol) was slowly added dropwise. The reaction was raised to 50 C. and stirred. After completion of the reaction, the reaction was dissolved with ethyl acetate (250 ml), and then extracted with water (3¡Á60 ml) to remove DMF, and washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, evaporated to dryness, and dried by pumping to provide a white solid 6 (1.475 g, 93.35%).

The chemical industry reduces the impact on the environment during synthesis 624-76-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; YANTAI UNIVERSITY; WANG, Hongbo; HONG, Xuechuan; ZHU, Xi; WANG, Pengyu; LV, Guangyao; FU, Jie; LUO, Huairong; ZHANG, Jianqiao; WEN, Meng; QU, Chunrong; ZHU, Jinmei; HU, Xianming; (7 pag.)US2016/102066; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

101335-11-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-chloro-4-fluoro-l-iodobenzene (10.0 g, 39.0 mmol) in dry THF (150 niL) was added /-PrMgCl (29.3 niL, 2.0 N, 58.5 mmol) dropwise at 0 C . After stirring for 1 hr at 0 C , the reaction was warmed to room temperature and stirred for 2 h. 1,4-cyclohexanedione monoethylene acetal (4.87 g, 31.2 mmol) was added and the reaction was stirred at room temperature for 12 h. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic phases were washed with brine (100 mL), then dried over Na2SO4. After concentration in vacuo, the crude material was purified by column chromatography (petroleum ethe?ethyl acetate = 5:1) on silica gel to give the desired product as a white solid (5.38 g, 48%). 1H NMR (400 MHz, CDCl3): delta 7.61-7.57 (m, IH), 7.14-7.11 (m, IH), 6.99- 6.94 (m, IH), 4.00-3.95 (m, AzU), 2.63-2.57 (m, IH), 2.42-2.36 (m, 2H), 2.17-2.10 (m, 2H), 2.05-2.01 (m, 2H), 1.72-1.69 (m, 2H).

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; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 64248-58-4 name is 1,2-Difluoro-4-iodobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

3,4-difluoro-iodobenzene (100mg, 0.41mmoL) and piperazine (32mg, 0.41mmoL) were mixed in 5mL of dioxane, under a nitrogen atmosphere, followed by triethylamine (54mg, 0.45mmoL), 2.5 mg of X-phos (2- dicyclohexyl-P-2 ‘, 4′, 6’-triisopropyl biphenyl) and 2.5mg of Pd2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) , then stirred at room temperature for 3 hours. Then vacuum to spin dioxane was added 20mL of water and 20mL of ethyl acetate, the organic phase was dried over sodium sulfate, spin dry and separate living give 37mg of product. The above product (37mg, 0.19mmoL) and piperazine (40mg, 0.55mmol), potassium carbonate (60mg, 0.43 mmol) were mixed in N, N- dimethylacetamide in a microwave at 150 stirred for 2 hours, and then spin to N, N- dimethylacetamide, purified by column to give (3-fluoro-4- (piperazin-1-yl) phenyl) dimethyl phosphine oxide (40mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Difluoro-4-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Hansoh BioMedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Yang, Fei; Zhang, Xiuchun; Sun, Xingyi; Wei, Mingsong; Wang, Chunjuan; Tong, Chaolong; Li, Chenghai; Bao, Rudi; Yu, Hongping; Xu, Yaochang; (52 pag.)CN105712928; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, The chemical industry reduces the impact on the environment during synthesis 116632-39-4, name is 5-Bromo-2-iodotoluene, I believe this compound will play a more active role in future production and life.

A Schienk tube was charged with compound 480 (402 mg, 1.31 MMOL) in 1,4-dioxane (3.0 mL), 5-BROMO-1-IODO-TOLUENE (358 mg, 1.19 MMOL), sodium tert-butoxide (160 mg, 1.67 MMOL), PD2 (dba) 3 (27 mg, 0.03 MMOL), and rac-BINAP (28 mg, 0.045 MMOL). The tube was capped with a rubber septum, flushed with argon for 5 min, and then stirred at 100 C for 72 h. The reaction mixture was allowed to cool to RT, and then poured into a mixture of water and EtOAc. The aqueous phase was extracted twice with more EtOAc. The combined organic phases were washed with brine, dried (MGSO4), filtered and concentrated in vacuo. The crude product was purified by chromatography eluting with petroleum ether/EtOAc 4: 1 to afford the title compound as yellow oil. 13C NMR (CI3) 8 195.4, 160.6, 147.7, 141.9, 137.7, 134.3, 134.0, 133.9, 133.4, 132.6, 131.6, 130.3, 130.0, 124.5, 117.6, 117.6, 116.1, 112.9, 111.0, 81.7, 67.0, 21.3, 17.8

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-iodotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

39998-81-7, 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. 39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene, A new synthetic method of this compound is introduced below.

Methyl-2-fluoro-4-iodo benzoate (Reagent G) A solution of 2-fluoro-4-iodo toluene (5 g, 26.6 mmol) in pyridine (2 mL) and water (20 mL) was treated with potassium permanganate (16.6 g, 105 mmol) and heated at 150 C. overnight. The reaction mixture was then cooled to room temperature and filtered and the filtrate was extracted with hexane. The aqueous phase was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was dissolved in 20 mL of methanol, treated with concentrated sulfuric acid (1 mL) and refluxed overnight. The volatiles were distilled off in vacuo and the residue was dissolved in diethyl ether, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title compound as an oil (0.26 g, 5%). 1H NMR (300 MHz, CDCl3):delta 7.60 (m, 4H), 3.93 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Allergan Sales, Inc.; US6252090; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

52548-14-8, The chemical industry reduces the impact on the environment during synthesis 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 5-methyl-2-iodobenzoic acid (3.0 g, 11 .4 mmol) in toluene (150 mL), SOCl2 (8.35 mL, 114 mmol) was added and the mixture was heated at 100C for 3 hours. Thesolvent was concentrated in vacuum and the residue was co-evaporated from toluene twice to give the title compound as a grey solid. Yield (3.2 g, 100%). 1H NMR (400 MHz, CDCl3): 6 2.42 (s, 3H), 7.09 (dd, 1 H), 7.90 (d, 1 H), 7.92 (d, 1 H).

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-5-methylbenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ROTTAPHARM SPA; STASI, Luigi Piero; ROVATI, Lucio; WO2013/139730; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2401-21-0, The chemical industry reduces the impact on the environment during synthesis 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, I believe this compound will play a more active role in future production and life.

PREPARATION 1 A mixture of p-aminoacetophenone (20 g), pyridine (11.7 g), and iodobenzene dichloride (40 g) in tetrahydrofuran (300 ml) was stirred for 5 hours at 0¡ã C. The insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. The residue obtained was crystallized from ethanol to give colorless crystals of 4′-amino-3′-chloroacetophenone (20.1 g). IR (Nujol): 3420, 3340, 3230, 1665, 1635, 1590 cm-1.

The chemical industry reduces the impact on the environment during synthesis 1,2-Dichloro-3-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4866091; (1989); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 455-13-0, name is 4-Iodobenzotrifluoride, 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 455-13-0, 455-13-0

General procedure: A 25 mL reaction flask was charged with copper nanoparticles (0.1 mmol)Aryl diiodonium (0.5 mmol),Benzene boronic acid (1.5 mmol),Potassium phosphate (1.0 mmol),Potassium fluoride (0.5 mmol), pivalic acid (0.5 mmol) and polyethylene glycol-400 (2.0 g)And the introduction of an atmospheric carbon monoxide.The reaction mixture was reacted at 100 C until the reaction was complete and cooled to room temperature,The product was isolated by column chromatography after evaporation of the solvent under reduced pressure.

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, 4-Iodobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Normal University; Han Wei; Cheng Laijing; Rong Qi; (9 pag.)CN103951537; (2017); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com