Author: Jessica.F

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. 58313-23-8, name is Ethyl-3-iodobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl-3-iodobenzoate

General procedure: A mixture of Pd2dba3·CHCl3 (6.2 mg, 2 mol%), Xantphos (14.0 mg,8 mol%), and ethyl 4-iodobenzoate (50.5 muL, 0.3 mmol) in THF (0.5mL) was stirred for 10 min at r.t. This mixture was added to a 0.105M solution of lithium tetrakis(ethoxycarbonylethynyl)indate in anhydrousTHF (3; 0.105 mmol) under a N2 atmosphere. The reactionmixture was heated at reflux for 3 h. After cooling to r.t., the reactionmixture was quenched with sat. aq NH4Cl (20 mL). The aqueouslayer was extracted with CH2Cl2 (3 × 20 mL), and the combinedorganic phases were sequentially washed with brine (3 × 20 mL),dried (MgSO4), filtered, and concentrated under reduced pressure.The residue was purified by column chromatography (silica gel,EtOAc-hexane, 1:20) to give 5a.

The synthetic route of 58313-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Youngchul; Kang, Dongjin; Jeon, Woo Hyung; Ryu, Taekyu; Lee, Phil Ho; Synthesis; vol. 46; 17; (2014); p. 2305 – 2311;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 41252-96-4, 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. 41252-96-4 name is 2-Chloro-1-iodo-4-nitrobenzene, 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.

(Step 1) Microflow system consisting of two T-type micromixers (M1, M2), two microtube reactors (R1, R2) and three tube precooling units (P1 (inner diameter ?=1 mm, length L=100 cm), P2 (?=1 mm, L=50 cm) and P3 (?=1 mm, L=100 cm)) was cooled to -20C. A solution (flow rate: 6.0 mL/min) of 2-chloro-1-iodo-4-nitrobenzene (2835 mg, 10 mmol) in THF (100 mL) and 0.4M phenyllithium in dibutyl ether and THF mixed solution (100 mL, 40.00 mmol) (flow rate: 2.25 mL/min) were introduced into M1 (?=0.5 mm) using syringe pump. The reaction solution was passed through R1 (?=1 mm, L=25 cm), and 0.6M chlorotrimethylsilane THF solution (100 mL, 60.00 mmol) (flow rate: 3.0 mL/min) was mixed in M2 (?=1 mm). The reaction solution was passed through R2 (?=1 mm, L=100 cm). After the reaction reached the static state, the solution containing a product was poured into water. The mixture was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0?5% ethyl acetate/hexane) to give (2-chloro-4-nitrophenyl)trimethylsilane (780 mg, 3.40 mmol, 34.0%) as a white solid. 1H NMR(300 MHz,DMSO-d6):delta0.40(9H,s),7.78(1H,d,J=8.3 Hz),8.13-8.17(1H,m),8.20(1H,d,J=2.3 Hz).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; FUKASE, Yoshiyuki; FUKUMOTO, Shoji; ODA, Tsuneo; TOKUHARA, Hidekazu; ISHII, Naoki; SASAKI, Yusuke; (255 pag.)EP3018123; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 19230-28-5, name is 1,3-Dichloro-2-iodobenzene, molecular formula is C6H3Cl2I, 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. Recommanded Product: 1,3-Dichloro-2-iodobenzene

Intermediate 34 4- (2, 6-Dichlorophenvl) butan-1-ol i) 4-(2, 6-Dichlorophenvl) but-3-yn-1-ol A solution of 1, 3-dichloro-2-iodobenzene (3.8g) in diethylamine (100mL) was treated with dichlorobis (triphenylphosphine) palladium (lI) (364mg) and copper iodide (199mg) and was heated at reflux. 3-Butyn-1-ol (962mg) was added and the reaction mixture was stirred at 80C for 16 h. The reaction mixture was then concentrated in vacuo. The residue was purified by chromatography (SPE, gradient from cyclohexane to dichloromethane) to give the title compound (2.2g) LCMS RT = 3.06 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19230-28-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/44787; (2005); 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 19230-28-5 as follows. Computed Properties of C6H3Cl2I

To a solution of 8-allyl-2- (methylthio) -5-oxo-5, 8- dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid (50 mg,0.18 mmol) in toluene (2 mL) and DMA (0.22 mL) was added1,3-dichloro-2-iodobenzene (98 mg, 0.36 mmol) and silver carbonate (49.7 mg, 0.18 mmol) . The suspension was degassed for 5 mm and (oxybis(2,1- phenylene))bis(diphenylphosphine) (9.7 mg, 0.018 mmol)and palladium (II) chloride (1.6 mg, 9.0 imol) added. The reaction mixture was then heated in a microwave (Biotage Initiator) at 150 C for 1 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (0-100%, EtOAc in cyclohexane) to affordthe title compound (12.4 mg, 18%) as a yellow solid. LCMS (Method A) : = 1.55 mi m/z = 378 [M+H].

According to the analysis of related databases, 19230-28-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ROUNTREE, James Samuel Shane; O’DOWD, Colin Roderick; BURKAMP, Frank; BELL, Mark Peter; WO2015/19037; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

General procedure: In a typical experiment, the alkene derivative (1.5 mmol), halobenzenesulfonyl chloride derivative (1 mmol), Li2CO3 (0.222 g, 3 mmol), and PdCl2(CH3CN)2 (12.9 mg, 0.05 mmol) were dissolved in 1,4-dioxane (2 mL) under an argon atmosphere. The reaction mixture was stirred at 100 C for 24 h. After evaporation of the solvent, the product was purified by silica gel column chromatography.

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:
Article; Skhiri, Aymen; Salem, Ridha Ben; Soule, Jean-Francois; Doucet, Henri; Synthesis; vol. 48; 18; (2016); p. 3097 – 3106;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, 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 2-Bromo-1-(4-iodophenyl)ethanone

[00212] (Based on J. Med. Chem. 2001, 44, 2990-3000) To a solution of Cbz-D-Ala-OH(5.0 g, 22.4 mmol) in NMP (100 mL) was added cesium carbonate (3.72 g, 11.4 mmol). After stirring at RT for 1 h, 12.2 (7.60 g, 22.4 mmol) was added. The reaction mixture was stirred at room temperature and monitored by LC/MS. The reaction solution was diluted with xylene (100 mL) and ammonium acetate (9.25 g, 120 mmol) and then stirred at 1200C for 4 hours. Up to 50 eq of additional ammonium acetate may be needed depending on the reaction progress. The key is to see solid in the flask at all times. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (200 mL). The EtOAc solution was washed with saturated sodium bicarbonate solution (200 mL) twice, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and stirred for 1 h to give a precipitate. Solid 12 (4.Og) was filtered off and dried under vacuum. The mother solution was concentrated by rotovap and the residue purified by preparative HPLC over silica gel to give additional 12 (Hex:EtOAc 1:1 to EtOAc 100%). The two products were combined and dried under vacuum to give a total of 5.8 g of 12 (58%).

The synthetic route of 31827-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOKINETICS, INC.; WO2007/56056; (2007); A2;,
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. 58313-23-8, name is Ethyl-3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl-3-iodobenzoate

General procedure: A dry and argon-flushed Schlenk tube, equipped with a magnetic stirring bar and a rubber septum was charged with Ni(acac)2 (12.8 mg, 0.05 mmol, 0.05 equiv) as catalyst, 4-fluorostyrene (24.4 mg, 0.20 mmol, 0.20 equiv), the aryl iodide or heteroaryl chloride 3 as electrophile (1.00 mmol, 1.00 equiv), and freshly distilled THF (1 mL). The resulting suspension was cooled to 0 C and the prior prepared bis-(aryl)manganese solution (0.70 mmol, 0.70 equiv) was added dropwise at the prior adjusted temperature. The reaction conversion was monitored by GC analysis of hydrolyzed aliquots. After full conversion of the electrophile, the reaction mixture was quenched with a sat. aq NH4Cl and extracted with EtOAc (3 × 75 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. Purification of the crude product by flash column chromatography afforded the desired products.

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 58313-23-8.

Reference:
Article; Benischke, Andreas D.; Desaintjean, Alexandre; Juli, Thomas; Cahiez, Gerard; Knochel, Paul; Synthesis; vol. 49; 24; (2017); p. 5396 – 5412;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 90347-66-3, 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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 3-iodo-4-methylbenzoate (0.2 g. 0.724 mmol) was added with bis-triphenylphosphine-palladium dichloride (25.424 mg, 0.036 mmol) and copper (1) iodide in absolute THF (3 mL) and triethylamine (1 mL) under inert gas. Thereafter, trimethylsilyl-ethyne was added at RT and the mixture was stirred overnight. For working up, the mixture was diluted with ethyl acetate, poured onto 0.5M ammonia solution and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with 0.5M hydrochloric acid and saturated sodium chloride solution, again extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was added with methanolic KOH (1 mL) and stirred for 2 hours at RT. The reaction mixture was diluted with ethyl acetate, poured onto 5% NaHCO3 solution and extracted twice with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 3-ethynyl-4-methylbenzoic acid.

The synthetic route of Methyl 3-iodo-4-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Apicore, LLC; Kovi, Ravishanker; Kannapan, Jayaraman; Thakor, Sanjay F.; Patel, Rajesh A; US2014/343282; (2014); 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. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-2-iodobenzoic acid

Schlenk reaction tube, 5-bromo-2-iodobenzoic acid (0.5 mmol), 3-mercapto 1,2,4-triazole (0.5 mmol), potassium carbonate (0.1 mmol) and HMPA (2 mL). The reaction tube was sealed and reacted at 80 C for 24 hours under an air atmosphere. After completion of the reaction, acetic acid (1 ml) was added, stirred at room temperature for 1 hour, then extracted twice with methylene chloride, and the organic layer was saturated with Brine, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. And purified by column chromatography to obtain the product 4, its structure and characterization data are as follows:

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; Chen Dingben; Taizhou University; Huang Ling; Lu Jiaming; (6 pag.)CN104788474; (2017); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 19230-28-5, A common heterocyclic compound, 19230-28-5, name is 1,3-Dichloro-2-iodobenzene, molecular formula is C6H3Cl2I, 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.

General procedure: (S)-3-((R)-Hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester 11a (250 mg, 0.9 mmol), copper(I) iodide (51 mg, 270 mumol), 1,10-phenanthroline (97 mg, 540 mumol) and 2,4-difluoro-1-iodobenzene (216 muL, 1.8 mmol) were combined in a vial under air. Toluene (1.4 mL, 14 mmol) was added, followed by the addition of cesium carbonate (587 mg, 1.8 mmol). Air was bubbled through the mixture, the vial was sealed, and the mixture was heated at 105C for 48 hours. The mixture was filtered through Celite. The Celite was then rinsed with DCM (2 x 15 ml), and the resultant filtrate was concentrated. The resultant oil was treated with 1.25 M of HCl in EtOH (5.8 mL, 7.2 mmol) and stirred overnight. The mixture was concentrated and purified by reverse phase preparative HPLC (10 to 70% CH3CN in water with 0.5% TFA) to yield 76 mg (97% purity, 26% yield) of the title compound as the mono-TFA salt.

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:
Article; Van Orden, Lori Jean; Van Dyke, Priscilla M.; Saito, D. Roland; Church, Timothy J.; Chang, Ray; Smith, Jacqueline A.M.; Martin, William J.; Jaw-Tsai, Sarah; Stangeland, Eric L.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1456 – 1461;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com