Month: June 2021

Reference of 69113-59-3, 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. 69113-59-3, name is 3-Iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 6: 3-ethynylbenzonitrile (0239) 3-Iodobenzonitrile (3.115 g) and copper iodide (103 mg) were mixed and tetrahydrofuran (13 mL) and triethylamine (3.0 mL) were added to the mixture which was stirred at room temperature. After degassing and purging with argon, dichloropalladium triphenylphosphine (191 mg) was added and degassed and purged with argon. To the mixture, ethynyl(trimethyl)silane (2.38 mL) was added dropwise and the mixture was stirred overnight at room temperature. The reaction solution was filtered through Celite and an organic layer was extracted by adding ethyl acetate and water. The resulting organic layer was washed with a saturated ammonium chloride aqueous solution and a sodium chloride solution, dried over anhydrous magnesium sulphate and concentrated. The obtained residue (3.11 g) was dissolved in methanol (20 mL) to which potassium carbonate (1.8 g) was added and the mixture was stirred at room temperature for 30 minutes. The reaction solution was filtered through Celite, washed with methyl tert-butyl ether and concentrated. The obtained residue was purified by a silica gel column (n-hexane : ethyl acetate = 100:0 ? 95:5) to give a titled compound (1.22 g) having the following physical properties. Properties: pale brown liquid; TLC (Rf): 0.40 (n-hexane : ethyl acetate = 13:1).

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

Reference:
Patent; Ono Pharmaceutical Co., Ltd.; ISHIDA, Akiharu; MATSUSHITA, Takeshi; SEKIGUCHI, Tetsuya; OKABE, Yasuyuki; KOMAGATA, Tatsuya; NISHIO, Takuya; (71 pag.)EP3053916; (2016); 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. 56404-21-8, name is 1-Iodo-2,4-dimethyl-3-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H8INO2

Step 2: To a hot suspension of iron powder (2.3 g, 8.3 mmol), ammonium chloride (2.16 g, 38.7 mmol) and water (18 ml.) in ethanol (50 ml.) was added 1-iodo-2,4- dimethyl-3-nitrobenzene in portions over a period of 10 minutes. The resulting mixture was heated at reflux for 1 hour, and filtered hot through a pad of Celite. The Celite was washed with ethanol and ethyl acetate and the filtrate was concentrated in vacuo. The residue was extracted with dichloromethane, the organics were dried over anhydrous sodium sulfate and filtered and the filtrate was evaporated to yield 2.Og (98%) of 3-iodo-2,6-dimethyl- phenylamine as a white solid. MS: 248.1 [M+H]+

According to the analysis of related databases, 56404-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; WO2009/108838; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 624-76-0,Some common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, molecular formula is C2H5IO, 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) Synthesis of compound (m-2) Under a nitrogen atmosphere, a three-necked flask equipped with a stirrer chip and a dropping funnel was charged with 20.9 g (200 mmol) of the compound (m-1), which was dissolved in 160 ml of dichloromethane. The dichloromethane solution was cooled to 0C and 30.4 g (300 mmol) of triethylamine was added, followed by further stirring. After adding 37.8 g (220 mmol) of ethanol diiodide dropwise over 30 minutes, the reaction solution was heated to room temperature and stirred for two hours. After the reaction, the reaction solution was added to 300 ml of saturated ammonia chloride water and the dichloromethane layer was extracted using a separating funnel. The remaining water layer was extracted twice with 200 ml of dichloromethane. After removing the solvent from the collected dichloromethane layer, the residue was separated using column chromatography to obtain a compound (m-2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodoethanol, its application will become more common.

Reference:
Patent; JSR Corporation; EP1961739; (2008); 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 25309-64-2 as follows. Application In Synthesis of 1-Ethyl-4-iodobenzene

General procedure: To a round-bottom flask were charged with an N?-Boc-N-aryl hydrazine 7 or 14 (48 mmol), 4-substituent iodobenzene 8 (40 mmol), CuI (0.78 g, 4 mmol), 1,10-phenanthroline (1.44 g, 8 mmol), Cs2CO3 (15.64 g, 48 mmol) and 40 mL of dry DMF at room temperature. The reaction mixture was degassed, charged with N2 gas and heated to 80 C. After 4-5 h, the resulting mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), filtered. The filtrate was then washed twice with brine (2×100 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, The residue was purified by flash chromatography with a mixture of petroleum ether and ethyl acetate as an eluent to afford the desired product, which was recrystallized from a mixture of petroleum ether and ethyl acetate to give the desired crystals 9 or 15.

According to the analysis of related databases, 25309-64-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Zhanhui; Hou, Shili; He, Wei; Cheng, Baoxiang; Jiao, Peng; Xu, Jiaxi; Tetrahedron; vol. 72; 17; (2016); p. 2186 – 2195;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 328-73-4, 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. 328-73-4 name is 1-Iodo-3,5-bis(trifluoromethyl)benzene, 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.

Palladium acetate (11.4 mg, 0.05 mmol), AgOAc (217 mg, 1.3 mmol), 3-methylbenzoic acid (136 mg, 1.0 mmol, 3,5-bis(trifluoromethyl)iodobenzene (1.02 g, 3.0 mmol and acetic acid (200 muL) were combined and heated at 120° C. for 4.5 h. After purification white solid was obtained, 207 mg (59percent), mp 217-219° C. (isooctane). Rf-0.60 (1/9 ethyl acetate-dichloromethane). 1H NMR (300 MHz, acetone-d6): delta 2.46 (s, 3H), 7.38-7.51 (m, 2H), 7.87 (s, 1H), 7.94 (s, 2H), 8.00 (s, 1H), 11.3 (brs, 1H). 13C NMR (75 MHz, acetone-d6) 320.6, 120.9 (br s), 124.2 (q, J-271.1 Hz), 129.7 (br s), 130.8, 131.1 (q, J-33.3 Hz), 131.5, 131.7, 133.1, 137.6, 139.3, 144.9, 168.0. FT-IR (neat, cm1) upsilon 1689, 1290, 1121. Anal. calcd for C16H10F6O2 (348.2 g/mol) C, 55.18; H, 2.89. Found: C) 55.07; H, 2.81. The 1H NMR and 13C NMR spectra are shown in FIGS. 24AB, respectively.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Iodo-3,5-bis(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF HOUSTON SYSTEM; US2009/12293; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 98-61-3,Some common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, molecular formula is C6H4ClIO2S, 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.

p-Iodobenzenesulfonyl chloride (9.08g, 0.03mol), 10mL acetonitrile and 30mL water were added into a 100-mL round-bottomed flask. Then around 15mL of NH3 gas was bubbled into the mixture. The solution was refluxed for 8h at 100C, and the volatile material was removed using a rotary evaporator. The solid crude product was then re-crystallized from a water solution and filtered. The pure product 7.64g of p-iodobenzenesulfonyl amide 1 was obtained with a yield of 90% after drying under high vacuum for 2h. (0015) Alternatively, in a 250-mL three-necked round bottom flask, p-iodobenzenesulfonyl chloride (9.08g, 0.03mol) was added. Then ca. 30mL of ammonia was condensed into the flask at -60C and the flask was allowed to slowly warm to room temperature over 8h. The crude product was washed with 40mL water and dried under the vacuum to give 8.07g purified amide 1 with a yield of 95%. 1H NMR (CD3CN, ppm): (ab, deltaa 7.89 (2H, d), deltab 7.60 (2H, d), Jab=10Hz, deltac 5.70 (2H, s) (0018) (note: The 1H for this and related compounds represents an aa?bb? spin system but it appears as a deceptively simple ab system with J/delta near 0.5. The deltaa,b for all compounds are taken as the midpoint of the second order doublets as an approximation as if it is a classic ab spin system. The Ja,b is assigned as that of a classic ab spin system. No effort was made to analyze the spectra further.)

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

Reference:
Article; Mei, Hua; Desmarteau, Darryl D.; Journal of Fluorine Chemistry; vol. 160; (2014); p. 12 – 15;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 6940-76-7, 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. 6940-76-7, name is 1-Chloro-3-iodopropane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of (+)-(2S,5R)-1-allyl-2,5-dimethylpiperazine (10.6 g, 68.7 mmol, prepared according to the literature procedure described by Janetka, J.W. et al., J. Org. Chem., 2003, 68, 3976-3980), 1 -chloro-3-iodo-propane (16.9 g, 82.8 mmol, 1.2 eq), and K2CO3 (24.6 g, 178 mmol, 2.6 eq) in acetone (230 mL) was heated at 5O0C for 16 hours. The mixture was cooled to room temperature, filtered through Celite, and the filtrate was concentrated in vacuo. Chromatography on silica gel using a gradient of 2M NHs/MeOH in CH2CI2 (0-2%) gave 14.05 g (89%) of (2S,5fi)-1 -allyl^^S-chloro-propyO^.delta- dimethyl-piperazine as a light yellow oil.To a solution of (2S,5/^-1-allyl-4-(3-chloro-propyl)-2,5-dimethyl-piperazine (14.05 g, 61 mmol) in anhydrous THF (78 mL) under argon was added thiosalicylic acid (10.33 g, 67 mmol, 1.1 eq) followed by the addition of a solution of tris(dibenzylidenacetone)-dipalladium (Pd2(dba)3, 2.8 g, 3.1 mmol, 5 mol%) and1 ,4-bis(diphenylphosphino)butane (DPPB, 1.33 g, 3.1 mmol, 5 mol%) in anhydrous THF (26 mL, pre-mixed for 15 minutes). After stirring at room temperature for 2 hours, the mixture was filtered through Celite. The filtrate was concentrated in vacuo and the residue was partitioned between 1 N aqueous HCI (70 mL) and Et2O (70 mL). The aqueous layer was separated and extracted with Et2O (50 mL x 2), and treated with NaOH (solid) to bring its pH to 13. The aqueous phase was extracted with CHCI3 (50 mL x 4). The combined organic phase was dried (Na2SO4) and concentrated in vacuo EPO to give 11.6 g (100%) of (2S,5/:?)-4-(3-chloro-propyl)-2I5-ciimethyl-piperazine as a light yellow oil.To a solution of (2S,5R)-4-(3-chloro-propyl)-2,5-dimethyl-piperazine (11.6 g, 61 mmol) in CH2CI2 (240 ml_) at O0C was added Boc2O (14.9 g, 67 mmol, 1.1 eq) and the mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was chromatographed on silica gel by eluting with 30% EtOAc/hexane to give 12.8 g (72%) of (2S,5fl)-4-(3-chloro-propyl)- 2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester as a light yellow oil. 1H NMR (300 MHz, CDCI3): delta 4.22 (m, 1 H), 3.64 (m, 3H), 3.23 (dd, J = 11.4, 3.9 Hz, 1 H), 2.55 (m, 1 H), 2.42 (m, 1 H), 2.22 (d, J = 11.4 Hz, 1 H), 1.87 (t, J = 6.3 Hz, 2H), 1.46 (s, 9H)7 1.21 (d, J = 6.9 Hz, 3H), 0.92 (d, J = 6.6 Hz, 3H).

The synthetic route of 1-Chloro-3-iodopropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/44293; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 62720-29-0, name is 1,3-Dibromo-5-fluoro-2-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H2Br2FI

Example 104k 2,6-Dibromo-4-fluorobenzaldehyde 104k To a solution of 1,3-dibromo-5-fluoro-2-iodobenzene (50 g, 132 mmol) in anhydrous toluene (300 mL) cooled at -35 C. was added a solution of isopropyl-magnesium chloride (84 mL, 171 mmol, 2.0M in Et2O) over 30 minutes while maintaining the internal temperature below -25 C. A clear brown solution was obtained and the stirring was continued for 1.5 h at -25 C. Then anhydrous DMF (34 mL, 436 mmol) was added over a period of 30 minutes. The reaction mixture was warmed to 10 C. (room temperature) over 1 h and stirred at this temperature for 1.5 h (hours). It was then quenched with 3.0M HCl and followed by the addition of ethyl acetate. The organic layer was separated and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (from 50:1 to 20:1) to give 104k as a white solid (20 g, 54%). 1H NMR (500 MHz, CDCl3) delta 10.23 (s, 1H), 7.48 (d, J=7.5, 2H).

The synthetic route of 62720-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Young, Wendy B.; US2013/116245; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile, molecular formula is C8H6IN, 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. COA of Formula: C8H6IN

iodophenyl cyanide(10 mmol, 2.28 g), Na2C03 (0.5 mmol, 57 mg)Soluble in tetrahydrofuran / water(Nu: nu = 3: 1) in a mixed solvent,After the reaction was stopped for 6 hours, the reaction was stopped. After allowing to stand at room temperature, the solvent was dried and usedSilica gel column chromatography to obtain a white solid after purification of p-iodobenzamide 2. 2 g (Yield: 89%);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51628-12-7, its application will become more common.

Reference:
Patent; Suzhou University of Science and Technology; ZHOU, YUYANG; WANG, XIAOMEI; YE, CHANGQING; ZHU, SAIJIANG; XU, PENGJIE; LIANG, ZUOQIN; (6 pag.)CN104016913; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 13329-40-3, 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. 13329-40-3, name is 1-(4-Iodophenyl)ethanone belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example QC-13a To a solution of 4-iodophenyl ethanone (14.76 g, 60.0 mmol) in 150 mL of dichloromethane was added bromine (9.5 g, 59.5 mmol) dropwise. The resulting solution was stirred at room temperature overnight. The solvent was removed under vacuum. The crude product was recrystallized with dichloromethane/hexanes to give Example QC-13a (11.8 g, 60.5%) as a grey solid. 1H NMR (500 MHz, CDCl3) delta ppm 4.38 (s, 2H) 7.68 (d, J=8.55 Hz, 2H) 7.86 (d, J=8.85 Hz, 2H); LC/MS: Anal. Calcd. for C8H771BrIO [M+H]+ 325.86; found 325.11.

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-(4-Iodophenyl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/249190; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com