Iodides-buliding-blocks

Synthetic Route of 116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Apparatus set-up: (0416) A 10 L 3 -necked round-bottomed flask, equipped with a mechanical overhead stirrer, reflux condenser, nitrogen inlet and exhaust. (0417) Experimental Procedure: (0418) Intermediate 3 (200 g, 0.644 mol) and intermediate 4 (190.9 g, 0.644 mol) were taken in 1, 2-dimethoxy ethane (2 L). (0419) Sodium carbonate solution (136.5 g, 1.288 mol, dissolved in 1 L of water) was added. (0420) The reaction mixture was degassed with nitrogen for an hour. (0421) Pd(PPh3)4 (7.44 g, 0.00644 mol) was added and heated at 100 C for 18 h. (0422) After completion of the reaction, it was filtered through a Florosil-silica plug and concentrated. (0423) The residue was dissolved in ethyl acetate (2 L), washed with water (1 L), brine (1 L), dried over sodium sulphate and concentrated. The crude product (200 g) was purified by silica column chromatography using hexane as an eluent to get 160 g of Intermediate D with 93 % HPLC purity. (0424) It was again purified by hot acetonitrile crystallization to get 135 g of Intermediate D with 97 % HPLC purity. (0425) It was further purified by hot acetonitrile crystallization to get 130 g of Intermediate D with 98.22 % HPLC purity. (0426) 130 g of Intermediate D at 98.22 % HPLC purity was crystallized with hot ethyl acetate/ methanol (1: 1.5) to get 100 g of Intermediate D with 98.9 % HPLC purity. (0427) 100 g of Intermediate D at 98.9 % HPLC purity was crystallized with hot ethyl acetate/ methanol (1: 1) to get 60 g of Intermediate D with 99.79 % HPLC purity. (0428) Filtrate obtained from all the above crystallizations were combined and concentrated to get 55 g at 97.2 % HPLC purity. (0429) 55 g of Intermediate D 97.2 % HPLC purity was crystallized with hot ethyl acetate/ methanol (1:0.8) to get 24 g of Intermediate D with 99.81 % HPLC purity. (0430) 24 g of Intermediate D at 99.81 % purity and 60 g of 99.79 % purity were combined, dissolved in dichloromethane (500 mL), heated to 45 C, filtered the hot solution and concentrated to get 80.5 g of Intermediate D with 99.70 % HPLC purity as white solid. (0431) ^-NMR (400 MHz, COCh): delta [ppm] 2.31 (s, 3H), 7.21 (d, / = 8.00 Hz, 1H), 7.40-7.45 (m, 2H), 7.48-7.52 (m, 3H), 7.89-7.91 (m, 2H), 8.07 (s, 1H), 8.15-8.17 (m, 1H).

The synthetic route of 5-Bromo-2-iodotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL CO., LTD; HUMPHRIES, Martin; TARRAN, William; KAMTEKAR, Kiran; STACKHOUSE, Philip; LEE, James; (76 pag.)WO2017/153731; (2017); A1;,
Iodide – Wikipedia,
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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. 289039-83-4, name is Methyl 2-amino-5-bromo-3-iodobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 2-amino-5-bromo-3-iodobenzoate

To a solution of methyl 2-amino-5-bromo-3-iodobenzoate (7.47 g, 20.99 mmol) in TEA (40 mL, 287 mmol) is added Pd(PPh3)2C12 (0.884 g, 1 .259 mmol), and copper(l) iodide (0.240 g, 1.259 mmol). The mixture is stirred under N2 for about 5 mm, and then trimethylsilylacetylene (3.83 mL, 27.3 mmol) is added. The mixture is stirred at rt for I h. The reaction is followed by LCMS (only 6% product after I h). The mixture is then transferred to a pressure tube and additional Pd(PPh3)2C12 (0.14 g, 0.199 mmol) and copper(l) iodide (0.036 g, 0.189 mmol) are added. The mixture is purged with N2 for 1 mm, and then it is heated at 60 C for 2 h (LCMS shows 54% mono-alkyne and 35% bis-alkyne). The reaction mixture is concentrated under reduced pressure. The residue is taken up in CH2CI2 and filtered through a plug of Celite. The Celite plug is washed with CH2CI2. The filtrate is washed with water (2x) and brine (lx), dried over Na2SO4, filtered and concentrated. The residue is chromatographed over silica gel (120 g ISCO column) eluting with 0-5% EtOAc/hexane gradient to yield a mixture of methyl 2-amino-5- bromo-3-((trimethylsilyl)ethynyl)benzoate and methyl 2-amino-3, 5- bis((trimethylsilyl)ethynyl)benzoate (4.2 to I ratio by I H NMR). LCMS (ES API) MH+ = 326 & 328 for Br isotopes mono-alkyne product; and LCMS (ES API) MH+ = 344 bis-alkyne product.A mixture of methyl 2-amino-5-bromo-3-((trimethylsilyl)ethynyl)benzoate (500 mg, 1 .53mmol; contaminated with 20% of methyl 2-amino-3,5-bis((trimethylsilyl)ethynyl)benzoate) and2 eq of Cul (584 mg, 3.07 mmol) in DMF (4 mL) is set under N2 and heated in a sealed tube at100 C for 80 mm. Upon cooling, the reaction mixture is diluted with Et20 and filtered through aplug of Celite. The Celite plug is washed with Et20 and EtOAc. The filtrate is concentrated underreduced pressure. The residue is chromatographed over silica gel eluting with 0-15% EtOAchexane gradient to give the title compound as a light yellow solid. LCMS (ES API) MH+ = 254 &256 for Br isotopes.

The synthetic route of 289039-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BECHERER, J. David; CADILLA, Rodolfo; DEATON, David Norman; HAFFNER, Curt; HENKE, Brad Richard; PREUGSCHAT, Frank; SCHULTE, Christie; (69 pag.)WO2016/87975; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, molecular formula is C7H4ClIO2, 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: 19094-56-5

Example 1 : Synthesis of the fluoride VIII.1Oxalylchloride (176kg; 1386mol; 1 ,14eq) is added to a mixture of 2-chloro-5-iodo benzoic acid (343kg; 1214mol) (compound IX.1 ), fluorobenzene (858kg) and N,N- dimethylformamide (2kg) within 3 hours at a temperature in the range from about 25 to 30C (gas formation). After completion of the addition, the reaction mixture is stirred for additional 2 hours at a temperature of about 25 to 30C. The solvent (291 kg) is distilled off at a temperature between 40 and 45C (p=200mbar). Then the reaction solution (91 1 kg) is added to aluminiumchloride AICI3 (181 kg) andfluorobenzene (192kg) at a temperature between about 25 and 30C within 2 hours. The reaction solution is stirred at the same temperature for about an additional hour. Then the reaction mixture is added to an amount of 570 kg of water within about 2 hours at a temperature between about 20 and 30C and stirred for an additional hour. After phase separation the organic phase (1200kg) is separated into two halves (600kg each). From the first half of the organic phase solvent (172kg) is distilled off at a temperature of about 40 to 50C (p=200mbar). Then 2-propanole (640kg) is added. The solution is heated to about 50C and then filtered through a charcoal cartouche (clear filtration). The cartouche may be exchanged during filtration and washed with a fluorobenzene/2-propanole mixture (1 :4; 40kg) after filtration. Solvent (721 kg) is distilled off at a temperature of about 40 to 50C and p=200mbar. Then 2-propanole (240kg) is added at a temperature in the range between about 40 to 50C. If the content of fluorobenzene is greater than 1 % as determined via GC, another 140kg of solvent are distilled off and 2-propanole (140kg) is added. Then the solution is cooled from about 50C to 40C within one hour and seeding crystals (50g) are added. The solution is further cooled from about 40C to 20C within 2 hours. Water (450kg) is added at about 20C within 1 hour and the suspension is stirred at about 20C for an additional hour before the suspension is filtered. The filter cake is washed with 2-propanole/water (1 :1 ; 800kg). The product is dried until a water level of <0.06%w/w is obtained. The second half of the organic phase is processed identically. A total of 410kg (94%yield) of product which has a white to off-white crystalline appearance, is obtained. The identity of the product is determined via infrared spectrometry. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19094-56-5, its application will become more common. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WEBER, Dirk; RENNER, Svenja; FIEDLER, Tobias; ORLICH, Simone; WO2011/39107; (2011); A1;,
Iodide – Wikipedia,
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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. 612-55-5, name is 2-Iodonaphthalene, A new synthetic method of this compound is introduced below., Formula: C10H7I

A mixture of 1,1-dibromo-1,2,2,2-tetrafluoroethane (260 mg), magnesium powder (50 mg) and tetrahydrofuran was added to a three-necked flask equipped with a stirrer and a condenser and replaced with nitrogen. 5 C After the reaction was stirred for 24 hours, the reaction was complete to obtain a solution of a trifluorovinylmagnesium complex. The solution was heated to 40 C and 2-iodonaphthalene (300 mg) and tetrakis (triphenylphosphine palladium) (11.5 mg) were added and the reaction was continued for 6 hours. The column was passed through n-hexane to give a colorless liquid, Yield 90%.

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; Beijing Yuji Science And Technology Co., Ltd.; Chen Chaohui; Jia Xiaoqing; Quan Hengdao; (5 pag.)CN106866355; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, 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. category: iodides-buliding-blocks

General procedure: A two-necked 200-mL round-bottomed flask equipped with a magnetic stirring bar was charged with aryl iodide 17 (1.733 g, 5.083 mmol), CuI (20.8 mg, 0.109 mmol), and DMF (25 mL). To the solution were added Et3N (2.1 mL, 15.1 mmol), PdCl2(PPh3)2 (36.1 mg, 0.0514 mmol), and trimethylsilylacetylene (1.1 mL, 7.8 mmol). The solution was stirred for 30 h. The reaction was quenched with water, and the mixture was extracted with EtOAc three times. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to leave the residue, which was purified by short silica gel column chromatography (hexanes-EtOAc= 9 : 1) to afford TMS-acetylene (1.706 g, 5.49 mmol, quant.) as yellow solids; Rf=0.74 (Silica gel, hexanes-EtOAc= 3 : 1). A 100-mL round-bottomed flask equipped with a magnetic stirring bar was charged with TMS-acetylene and MeOH (10 mL). To the solution was added K2CO3 (1.4 g, 10.1 mmol) at 0 C. The solution was stirred for 10 min. The solution was concentrated under reduced pressure. The reaction mixture was filtered through a pad of Celite. The filter cake was washed with ether, and the filtrate was concentrated under reduced pressure to leave the residue, which was purified by silica gel column chromatography (hexanes-ether= 9 : 1) to afford aryl acetylene 18 (909 mg, 3.80 mmol, 75 % for 2 steps) as a pale yellow solid;

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cho, Hidetsura; Iwama, Yusuke; Okano, Kentaro; Tokuyama, Hidetoshi; Chemical and Pharmaceutical Bulletin; vol. 62; 4; (2014); p. 354 – 363;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 63262-06-6, name is 1,4-Dibromo-2,5-diiodobenzene, molecular formula is C6H2Br2I2, 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. Computed Properties of C6H2Br2I2

Under the protection of nitrogen, 4.85 g of compound II, 2.50 g of trimethylsilylacetylene, 50 ml of triethylamine, 100 mg of cuprous iodide and 150 mg of dichlorobis(triphenylphosphine)palladium were added.Block the reaction system, stir at room temperature overnight, gas phase detectionReaction process, after the reaction is over,The triethylamine was distilled off under reduced pressure, and the column was eluted with a solvent of n-hexane to afford a crude product.White solid 3.2 g, yield 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 63262-06-6, its application will become more common.

Reference:
Patent; Henan Academy Of Sciences Chemical Institute Co., Ltd.; Zhou Yang; Zhao Yongde; Dai Bencai; Liu Changchun; Wang Lantian; Zhang Yuli; Chai Cuncai; Chen Jieying; (11 pag.)CN108558948; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 175278-11-2, These common heterocyclic compound, 175278-11-2, name is 1-Bromo-3,5-difluoro-2-iodobenzene, 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.

Step 3. Ethyl 2-(2′-bromo-4′,6′-difluoro-2,3,4,5-tetrahydro-[l,l’-biphenyl]-4-yl)acetate. In a sealed microwave tube, a mixture of ethyl 2-[4-(tetramethyl-l,3,2-dioxaborolan-2- yl)cyclohex-3-en-l-yl] acetate (200 mg, 0.68 mmol), [1,1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.9 mg, 0.03 mmol), l-bromo-3,5- difluoro-2-iodobenzene (260 mg, 0.82 mmol) and sodium carbonate (0.85 mL, 2.0 M, 1.7 mmol) in dioxane (3.40 mL) was heated at 70C for 20 h. Upon completion of the reaction, the reaction mixture was filtered through celite, washed thoroughly with EtOAc, and purified via flash chromatography (0-20% EtOAc/heptanes) to obtain the title compound as a colorless oil (210 mg, 86%). 1H NMR (400 MHz, CDCb) d 7.13 (td, /= 2.0, 8.1 Hz, 1H), 6.78 (dt, / = 2.5, 8.8 Hz, 1H), 5.60 (d, / = 1.7 Hz, 1H), 4.17 (q, / = 7.2 Hz, 2H), 2.45 – 2.31 (m, 3H), 2.22 – 2.12 (m, 1H), 2.00 – 1.84 (m, 2H), 1.63 – 1.50 (m, 1H), 1.48 (s, 2H), 1.28 (t, / = 7.1 Hz, 3H). [M+H] = 361.0.

Statistics shows that 1-Bromo-3,5-difluoro-2-iodobenzene is playing an increasingly important role. we look forward to future research findings about 175278-11-2.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, THOMPSON, Jillian; BOOKSER, Brett; BURLEY, Scott; GARCIA-REYNAGA, Pablo; HUDSON, Andrew; PETERS, Marco; PRATT, Benjamin; THOMPSON, Aaron; TRAN, Joe; VALDEZ, Lino; (211 pag.)WO2019/168866; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 148870-57-9, 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. 148870-57-9 name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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.

Example 6 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one Based on EP 0 534 859 A solution of the (d) camphorsulphonate salt obtained in Example 5 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. Yield=64%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Les Laboratoires Servier; Vaysse-Ludot, Lucile; Le Flohic, Alexandre; Vaultier, Michel; Pucheault, Mathieu; Kaminski, Thomas; US8859763; (2014); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 71838-16-9,Some common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, molecular formula is C7H6BrI, 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: Method B: To a 10 mL sealed vial was added Cu(OAc)2·H2O (20 mg, 0.1 mmol), N-methoxy-1H-pyrrole-2-carboxamide (14 mg, 0.1mmol), aryl halide (1.0 mmol), aminobenzenethiol (1.2 mmol), KOH (224 mg, 4.0 mmol), PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 C for 15 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 40 mL) and water (40 mL). The combined organic phases were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-iodo-4-methylbenzene, its application will become more common.

Reference:
Article; Huang, Manna; Hou, Jianying; Yang, Ruiqiao; Zhang, Liting; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 24; (2014); p. 3356 – 3364;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 660-49-1, A common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-iodoaniline, molecular formula is C6H5FIN, 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.

A solution of 3-fluoro-5-iodoaniline (250 mg, 1.055 mmol) and dihydro-2H- pyran-4(3H)-one (264 mg, 2.637 mmol) in methanol (5 mL) was charged into a 25 mL round bottom flask with a magnetic stir bar. Acetic acid (0.121 mL, 2.11 mmol) was added and the resulting solution was stirred for 30 minutes at room temperature. Sodium cyanoborohydride (133 mg, 2.11 mmol) was added, the resulting solution was stirred overnight at room temperature. The reaction was quenched with 10 mL 1M aqueous NaOH, stirred for 15 minutes. The solution was extracted with EtOAc (3 x 15 mL), the combined organic layers were washed with brine (15 mL), dried with MgS04, filtered, and evaporated under vaccuum. The crude product was dry loaded onto 3 g. silica and purified by column chromatography (ISCO normal phase, 24 g. gold column, 0-60% EtOAc/hexanes gradient) to isolate N-(3-fluoro-5-iodophenyl)tetrahydro-2H-pyran-4- amine (047) (208 mg, 0.648 mmol, 61%). 1H NMR (400 MHz, CDCb) d ppm 1.41 – 1.55 (m, 2 H) 1.95 – 2.09 (m, 2 H) 3.38 – 3.48 (m, 1 H) 3.53 (td, 7=11.61, 2.13 Hz, 2 H) 3.65 – 3.80 (m, 1 H) 4.02 (br d, 7=11.54 Hz, 2 H) 6.20 – 6.30 (m, 1 H) 6.73 (br d, 7=1.76 Hz, 2 H). LCMS: 322.6 [M+H]+.

The synthetic route of 660-49-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COOK, Andrew; REYNOLDS, Dominic; ZHONG, Cheng; BRAWN, Ryan; ELLERY, Shelby; SAMARAKOON, Thiwanka; LIU, Xiang; PRAJAPATI, Sudeep; SHEEHAN, Megan; LOWE, Jason T.; PALACINO, James; (378 pag.)WO2019/200100; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com