Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 13697-89-7, name is 1,3-Difluoro-2-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 13697-89-7, COA of Formula: C6H3F2I

B 5-Fluoro-1,4-dihydro-1,4-methano-naphthalene A solution of 2,6-difluoroiodobenzene (5.0 g. 20.8 mmol) and cyclopentadiene (2.07 g, 31.3 mmol) was stirred at 0 C. in P ether (70 mL, 40-60 C.) under N2 and treated with n-BuLi (8.74 mL, 2.5M in hexanes, 21.8 mmol) dropwise over 10 minutes. The reaction was quenched after 15 minutes by addition of aqueous 1N HCl solution and the product was extracted with hexanes (3*50 mL). The combined organic layer was washed with H2O (50 mL), saturated aqueous NaCl solution (50 mL), dried (MgSO4), filtered and evaporated Chromatography on Silica gel provided product as an oil (1.5 g, 45%) (TLC hexanes Rf 0.55). 1H NMR (400 MHz, CDCl3) delta 7 08 (ddd, J=7.0,1.0,0.8 Hz, 1H), 6.96 (ddd, J=8.5,8.3,7.0 Hz, 1H), 6.86 (br s, 2H), 6.72 (ddd, J=8.5,8.3,0.8 Hz, 1 H), 4.25 (br s, 1H), 3.98 (br s, 1H), 2.36 (ddd, J=7.2,1.7,1.7 Hz, 1H), 2.30 (ddd, J=7.2,1.7,1.5 Hz, 1H). GCMS m/e 160 (M+).

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-2-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wadsworth, Jotham; Palmer, Paige Roanne; US2002/72524; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 2786-00-7, name is 5-Iodo-2-methoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Iodo-2-methoxybenzoic acid

General procedure: A solution of 3-iodobenzoic acid (4.6 g, 18.5 mmol, 1.0 equiv) and triethylamine (3.78 g,37.1 mmol, 2 equiv) in anhydrous dichloromethane (150 mL) was allowed to stir at room temperature for 10 min under a nitrogen atmosphere. The mixture was cooled to 0 C, and after 30 min, thionyl chloride (20.4 mmol, 1.1 equiv) was added dropwise and allowed to stir for 1.5 h. The reaction mixture was brought to room temperature, with continued stirring for 30 min followed by concentration by rotary evaporation.

According to the analysis of related databases, 2786-00-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brummel, Beau R.; Giambalvo, Lauren N.; Gross, Kristopher G.; Kobra, Khadijatul; Lex, Timothy R.; McMillen, Colin D.; Panda, Soham; Pennington, William T.; Swasy, Maria I.; Whitehead, Daniel C.; Tetrahedron Letters; (2020);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 51839-15-7, 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. 51839-15-7 name is Dimethyl 5-iodoisophthalate, 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.

General procedure: A 15 mL heavy walled pressure tube sealable with a gasketed Teflon screwcap was charged with a diaryl iodonium triflate (0.2 mmol, 1 equiv), an aryl iodide (1.0 mmol, 5 equiv.), and 1,2-dicholoroethane (2 mL, 0.1 M iodonium triflate concentration). The tube was sealed (Teflon screw cap) and immersed in an oil bath maintained at 80 C. After the indicated time, the tube was retrieved and cooled to rt and the contents were concentrated under reduced pressure. The crude material was purified by silica gel flash chromatography (gradient 10 ? 50% acetone/CH2Cl2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl 5-iodoisophthalate, and friends who are interested can also refer to it.

Reference:
Article; Racicot, Leanne; Ciufolini, Marco A.; Tetrahedron; vol. 73; 50; (2017); p. 7067 – 7072;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 689260-53-5, name is 2-Bromo-5-iodo-1,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8BrI

Under an argon atmosphere, Intermediate 6 (1.20 g, 2.40 mmol), 2-Bromo-5-iodo-1,3-dimethylbenzene (Intermediate 15) (893 mg, 2.88 mmol)(1.68 g, 4.80 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) and copper iodide (91.4 mg, 0.48 mmol, 0.35 mmol) were added to a solution of L-proline (110 mg, 0.96 mmol; manufactured by Wako Pure Chemical Industries, (Manufactured by Wako Pure Chemical Industries, Ltd.) Dimethylformamide (2.4 ml, manufactured by Wako Pure Chemical Industries, Ltd.) was heated to 110 C under an argon atmosphere for 48 hours. to the next,After cooling to room temperature, saturated aqueous ammonium chloride solution (30 ml) and dichloromethane (100 ml) were added to the reaction mixture and the layers were separated. The organic layer was dried over magnesium sulfate and the residue was purified by silica gel column chromatography (dichloromethane 20% Hexane 80%) to obtain Intermediate 16 as pale yellow crystals (1.49 g, yield 91%).

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 689260-53-5.

Reference:
Patent; Kokuritsu Daigaku Hojin Kyushu Daigaku; Kaji, Hironori; Suzuki, Hajime; Suzuki, Katsuaki; Oheiwa, Hajime; Wakamiya, Atsushi; Fukushima, Tatsuya; Suzuki, Huritz; Murata, Yaseujiro; Sieje, Kacheuyuki; Adachi, Jihaya; (48 pag.)KR2015/123907; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, 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. Formula: C8H9IO2

General procedure: Rh(PPh3)3Cl (2.5 mol%) and DPPP (0.04 mmol) were transferred into an oven-dried tube(15 mL), which was evacuated and backfilled with N2 (5x). THF(2 mL), H2O (1 mmol), aryl iodides (1.2 mmol), furfural (1 mmol)and amine (1.8 mmol) were added into the tube via syringe and sealed with Teflon plug. The reaction mixture was stirred at 140 C for 12 h. After the reaction was complete, the mixture was concentrated by rotary evaporation. The crude product was purified by column chromatography (EA/PE = 1/20) on a silica gel to afford the desired product.

The synthetic route of 5460-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qi, Xinxin; Zhou, Rong; Ai, Han-Jun; Wu, Xiao-Feng; Journal of Catalysis; vol. 381; (2020); p. 215 – 221;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

10297-05-9, name is 1-Chloro-4-iodobutane, 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. Computed Properties of C4H8ClI

4-Chloro-1-(3-pyridyloxy)butane Under a nitrogen atmosphere, a solution of 3-hydroxypyridine (3.50 g, 36.8 mmol) in N,N-dimethylformamide (DMF) (10 mL) was added drop-wise over 5 min to a cold (0-5° C.), stirring slurry of sodium hydride (1.16 g of an 80percent dispersion in mineral oil, 38.6 mmol) in DMF (40 mL). The mixture was allowed to stir and warm to ambient temperature over 1 h. The mixture was then cooled to 0-5° C., and 1-chloro-4-iodobutane (9.67 g, 44.2 mmol) was added drop-wise over 5 min. The resulting dark-brown mixture was stirred at ambient temperature for 2 h. Water (25 mL) was added, followed by saturated NaCl solution (25 mL), and the mixture was extracted with ether (4*50 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a residue that was dried briefly under high vacuum to give 6.89 g (quantitative yield) of an oil.

The synthetic route of 10297-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DULL, GARY MAURICE; REICH, ERIN E.; WAGNER, JARED MILLER; BHATTI, BALWINDER SINGH; CONSILVIO, MICHAEL B.; US2001/31771; (2001); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 54507-44-7,Some common heterocyclic compound, 54507-44-7, name is 2-Iodo-4-(trifluoromethyl)benzoic acid, molecular formula is C8H4F3IO2, 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.

Intermediate AI: S-trifluoromethyl-biphenyM-carboxylic acidA mixture of 2-iodo-4-trifluoromethyl-benzoic acid (CAS: 54507-44-7) (300 mg, 0.949 mmol) phenylboronic acid (239 mg, 1.898 mmol), sodium carbonate (302 mg, 2.847 mmol) and palladium (II) acetate (10.7 mg, 0.0475 mmol) in 4.5 ml water was stirred at room temperature for 48 hours. The mixture was filtered and the filtrate was acidified with HCl 37%. The mixture was stirred at room temperature for 30 minutes. The solid was filtered, washed with water and dried in vacuo to provide 225 mg (89 %) of the title compound as a brown solid. MS(m/e): 264.9 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-4-(trifluoromethyl)benzoic acid, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; KOLCZEWSKI, Sabine; PINARD, Emmanuel; WO2011/23667; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 61272-76-2, 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. 61272-76-2, name is 4-Fluoro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To the solution of o-iodoaniline derivatives (1.00 mmol) in pyridine methanesulfonyl chloride (1.00 mmol) was added and the reaction mixture was stirred at r.t. for 2 h. Water (100 ml) was then added, and the solution was extracted with ethyl acetate (3 x 10 ml). The organic extracts were washed with water (4 x 50 ml) and brine (50 ml), dried over Na2SO4 and the solvent was distilled off to furnish a viscous mass that was purified by column chromatography on silica gel to get compound 17

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-2-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Debnath, Sudarshan; Mondal, Shovan; Tetrahedron Letters; vol. 59; 23; (2018); p. 2260 – 2263;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 117832-17-4, name is 2-Iodo-4,5-dimethylaniline, 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 117832-17-4, Application In Synthesis of 2-Iodo-4,5-dimethylaniline

60.8 g of lithium chloride is added to a solution of 15.5 g of [1,4]-benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Than a solution of 35.1 g of 2-iodo-4,5-dimethylaniline (prepared according to J. Med. Chem. 2001, 44, 3856-3871) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-d6 (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1H, d); 5.18 (2H, s); 7.23 (1H, s); 7.30-7.45 (5H, m); 7.59 (1H, s); 7.72 (1H, dd); 10.05 (1H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-4,5-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; US2012/277205; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 400-97-5, name is 1-Iodo-2-nitro-4-(trifluoromethyl)benzene, 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 400-97-5, Recommanded Product: 400-97-5

b Preparation of 2-amino-4-trifluoromethyliodobenzene: A mixture of 225 ml of water, 166 g of iron and 10.03 g of ammonium chloride are heated to reflux. 317 g of 2-nitro-4-trifluoromethyliodobenzene are added thereto over a period of 2 hours, then refluxing is continued for 3 hours 30 minutes when the addition is complete. The whole is allowed to cool then the medium is extracted 4 times with 250 ml of benzene each time. The mixture is then filtered and subsequently decanted. The organic layer is dried and the solvent is evaporated. After distillation, 256 g of 2-amino-4-trifluoromethyliodobenzene are recovered, b.p.: 102 to 114 C., ind (25 C.): 1.556. (Yield: 89.5%).

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; Adir et Compagnie; US5079245; (1992); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com