Month: November 2020

628-21-7, A common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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.

In a 250 mL three-necked flask was added 19.4 g of anthrone (0.1 mol), 150 mL of dry THF, under stirring, 34. 1 g of 1,4-diiodobutane (0.1 1 mol) and 26.8 g of potassium tert-butoxide (0.24 mol) the reaction was stirred at room temperature for 3 h and refluxed for 3 h. The reaction was quenched by the addition of saturated ammonium chloride solution, extracted with ethyl acetate, separated by column chromatography, and 13.6 g of white solid B-I was obtained by column chromatography. The yield was 55%

The synthetic route of 628-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kunshan Weixinnuo Display Co., Ltd.; Tsinghua University; Beijing Weixinnuo Technology Co., Ltd.; Qiu Yong; Fan Hongtao; (61 pag.)CN103508940; (2017); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, Name is 1,2-Difluoro-4-iodobenzene, 64248-58-4, 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.

Example 24 (E)-4-Cyclopentyl-2-(3,4-difluoro-phenyl)-but-2-enoic acid thiazol-2-ylamide A mixture of zinc dust (0.98 g, 15 mmol, Aldrich, -325 mesh) and dry tetrahydrofuran (3 ML) under argon was treated with 1,2-dibromoethane (0.14 g, 0.75 mmol).. The zinc suspension was then heated with a heat gun to ebullition, allowed to cool, and heated again.. This process was repeated three times to make sure the zinc dust was activated.. The activated zinc dust suspension was then treated with trimethylsilyl chloride (82 mg, 0.75 mmol), and the suspension was stirred for 15 min at 25 C. The reaction mixture was then treated dropwise with a solution of (E)-4-cyclopentyl-2-iodo-but-2-enoic acid methyl ester (prepared in Example 21, 1.47 g, 5 mmol) in dry tetrahydrofuran (1.5 ML) over 3 min.. After the addition, the reaction mixture was stirred for 1 h at 40-45 C. and then stirred overnight at 25 C. The reaction mixture was then diluted with dry tetrahydrofuran (5 ML), and the stirring was stopped to allow the excess zinc dust to settle down (~2 h).. In a separate reaction flask, bis(dibenzylideneacetone)palladium(0) (54 mg, 0.1 mmol) and triphenylphosphine (104 mg, 0.4 mmol) in dry tetrahydrofuran (10 ML) was stirred at 25 C. under argon for 10 min and then treated with 3,4-difluoro-iodobenzene (0.96 g, 4 mmol) and the freshly prepared zinc compound in tetrahydrofuran.. The resulting brick red solution was heated at 25 C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material.. The reaction mixture was cooled to 25 C. and then poured into a saturated aqueous ammonium chloride solution (50 ML), and the organic compound was extracted into diethyl ether (2*50 ML).. The combined ether extracts were washed with a saturated aqueous sodium chloride solution (1*50 ML), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo.. Biotage chromatography (FLASH 40M, silica, 4/1 hexanes/diethyl ether) afforded (E)-4-cyclopentyl-2-(3,4-difluoro-phenyl)-but-2-enoic acid methyl ester (0.82 g, 73%) as a viscous oil: EI-HRMS m/e calcd for C16H18F2O2 (M+) 280.1275, found 280.1275.

Statistics shows that 1,2-Difluoro-4-iodobenzene is playing an increasingly important role. we look forward to future research findings about 64248-58-4.

Reference:
Patent; Hoffmann-La Roche Inc.; US6353111; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 915095-86-2, name is (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone, 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 915095-86-2, 915095-86-2

Example 2: Synthesis of the ketone VII.1To a solution of the fluoride VIII.1 (208kg), tetrahydrofuran (407kg) and (S)-3- hydroxytetrahydrofuran (56kg) is added potassium-terf-butanolate solution (20percent) in tetrahydrofuran (388kg) within 3 hrs at 16 to 25¡ãC temperature. After completion of the addition, the mixture is stirred for 60min at 20¡ãC temperature. Then the conversion is determined via HPLC analysis. Water (355kg) is added within 20 min at a temperature of 21 ¡ãC (aqueous quench). The reaction mixture is stirred for 30 min (temperature: 20¡ãC). The stirrer is switched off and the mixture is left stand for 60 min (temperature: 20¡ãC). The phases are separated and solvent is distilled off from the organic phase at 19 to 45¡ãC temperature under reduced pressure. 2- Propanol (703kg) is added to the residue at 40 to 46¡ãC temperature and solvent is distilled off at 41 to 50¡ãC temperature under reduced pressure. 2-Propanol (162kg) is added to the residue at 47¡ãC temperature and solvent is distilled off at 40 to 47¡ãC temperature under reduced pressure. Then the mixture is cooled to 0¡ãC within 1 hr 55 min. The product is collected on a centrifuge, washed with a mixture of 2- propanol (158kg) and subsequently with terf.-butylmethylether (88kg) and dried at 19 to 43¡ãC under reduced pressure. 227kg (91 ,8percent) of product are obtained as colourless solid. The identity of the product is determined via infrared spectrometry.

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, (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WEBER, Dirk; RENNER, Svenja; FIEDLER, Tobias; ORLICH, Simone; WO2011/39107; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

608-28-6, 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. 608-28-6 name is 2-Iodo-1,3-dimethylbenzene, 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 10-mL glass vessel equipped with J. Young O-ring tap containing a magnetic stirring bar was flame-dried under vacuum and filled with argon after cooling to room temperature. To this tube were added 2-substituted 2H-indazole (1: 0.40 mmol), CuI (7.6 mg, 0.04 mmol), 1,10-phenanthroline (7.2 mg, 0.04 mmol), LiOt-Bu (64 mg, 0.80 mmol), and haloarene (2: 0.80 mmol), followed by DMF (0.5 mL) under a stream of argon. The tube was sealed with O-ring tap, and then heated at 110 C for 15 h in an eight-well reaction block with stirring. After cooling the reaction mixture to room temperature, the mixture was passed through a short pad of Celite (EtOAc). The filtrate was concentrated and the residue was subjected to preparative HPLC (acetonitrile/water as an eluent) to afford the arylated product 3.

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:
Conference Paper; Hattori, Keika; Yamaguchi, Kazuya; Yamaguchi, Junichiro; Itami, Kenichiro; Tetrahedron; vol. 68; 37; (2012); p. 7605 – 7612;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

124700-41-0, The chemical industry reduces the impact on the environment during synthesis 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid, I believe this compound will play a more active role in future production and life.

Add bis (triphenylphosphine) palladium (II) dichloride (70 mg, 0. 10 mmol), copper (I) iodide (38 mg, 0. 20 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (400 mg, 3. 0 mmol) to a solution of 2-fluoro-5-iodobenzoic acid (0. 53 g, 2. 0 mmol) in triethylamine (4. 2 mL, 30. 0 mmol) and stir at room temperature for 1 h. Heat at 50 C for 18 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100 : 0 to 60 : 40 ethyl acetate : methanol. Triturate the resulting solid with 3 : 1 hexanes : methanol to give the title compound as an off-white solid (295 mg, 54%). 1H NMR (300 MHz, DMSO-d6) 6 3. 86 (s, 3H), 7. 09-7. 17 (m, 1H), 7. 46-7. 53 (m, 1H), 7. 55-7. 59 (m, 1H), 7. 81-7. 87 (m, 1H), 8. 24-8. 35 (m, 2H) ; MS (APCI) : m/z = 272 [M+H] +.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, molecular formula is C8H7IO2, 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. 82998-57-0

To a solution of 3-iodo-4-methyl-benzoic acid (10.0 g, 38.2 mmol) in methanol (70 ml) is added concentrated sulfuric acid (0.5 ml). The reaction mixture is heated at 70 C. for 48 hours, cooled to room ambient temperature and then concentrated. After that, ethyl acetate (100 ml) and aqueous NaHCO3 (saturated, 100 ml) solution are added to the residue. The organic layer is separated and washed again with aqueous NaHCO3 (saturated, 100 ml) solution. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to yield 3-iodo-4-methyl-benzoic acid methyl ester 1. It is used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1H), 7.87 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=8.4 Hz), 3.85 (s, 3H), 3.35 (s, 3H); LC-MS m/z: 277.0 (M+1).

The chemical industry reduces the impact on the environment during synthesis 3-Iodo-4-methylbenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IRM LLC; US2009/203666; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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. 64248-58-4.

General procedure: A vial was charged with 2-Hydroxy-4-methoxybenzaldehyde (1.97 mmol, 300 mg), PdCl2 (5 mol%, 17.5 mg), 1,2-Difluoro-4-iodobenzene (2 equiv., 946.7 mg), Na2CO3 (2 equiv., 418.1 mg), LiCl (0.4 equiv., 16.7 mg), and DMF (19.7 mL, 0.1 M of the aldehyde), purged with N2 and stirred at 110 C 4-10 h. The reaction was monitored with LC-MS and TLC (TLC conditions: Aliquot was diluted with CH3OH, eluted with EtOAc/heptane 1:3, and stained with 2,4- dinitrophenylhydrazine solution). The reaction mixture was filtered over a pad of Celite, diluted with EtOAc, washed 3 times with water, and the aqueous layers was acidified and extracted twice with EtOAc. The combined organic layers was dried over Na2SO4, concentrated and purified on silica using EtOAc/Heptane 1:20 ? 1:9 step gradient) to afford 2′-hydroxybenzophenone in 69.3% yield. (NMR data is given in the supporting information).

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

Reference:
Article; Saleeb, Michael; Mojica, Sergio; Eriksson, Anna U.; Andersson, C. David; Gylfe, Asa; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1077 – 1089;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

112671-42-8, 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. 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows.

9.9-dimethyl acridine (10 g, 47.8 mmol) under nitrogen4-bromo-1-iodo-2-nitrobenzene (32.74 g, 99.85 mmol),Potassium carbonate (13.8 g, 99.85 mmol), copper (6.35 g, 99.85 mmol),Ethylene glycol (350 ml) was stirred, and the reaction was stirred at about 100 C for about 1 hour.It was extracted with acetone, and the organic layer was taken, and a hydrochloric acid solution (hydrochloric acid: deionized water = 1:10 vol.%) (500 ml) was added.After washing with deionized water,Recrystallization of acetone and methanol,Intermediate 1-1 (12 g, 59%) was obtained.

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; Jilin Aolaide Optoelectric Materials Co., Ltd.; Jin Furong; He Jinxin; Wang Shikai; (16 pag.)CN108727374; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

696-41-3, name is 3-Iodobenzaldehyde, 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. 696-41-3

To a mixture of compound 1 (326 mg, 2.5 mmol), compound 214 (582 mg, 2.5 mmol), and PdCl2(PPh3)2 (37 mg, 0.05 mmol) in a flame-dried Schlenk tube were added THF (15 mL) and Et3N (5 mL) under argon atmosphere and followed by the addition of CuI (10 mg, 0.05 mmol) 10 min later. The mixture was stirred at room temperature for 9 h and then water (20 mL) and brine (20 mL) were added. After being extracted with ethyl acetate (3¡Á30 mL), the combined organic phase was washed with brine and dried over sodium sulfate. Upon removal of the solvent under reduced pressure, the resulting residue was purified by column chromatography (petroleum ether/dichloromethane 1:1) to give compound 3 as a pale yellow solid (487 mg, 83%). Mp 77-78 C. 1H NMR (300 MHz, CDCl3): delta 7.49 (t, J=7.2 Hz, 1H), 7.54-7.64 (m, 2H), 7.67 (d, J=7.5 Hz, 1H), 7.81 (d, J=7.5 Hz, 1H), 7.90 (d, J=7.5 Hz, 1H), 7.96 (d, J=7.5 Hz, 1H), 8.07 (s, 1H), 10.03 (s, 1H), 10.63 (s, 1H). 13C NMR (100 MHz, CDCl3): delta 86.4, 94.5, 123.6, 126.0, 127.6, 129.1, 129.3, 129.7, 132.9, 133.4, 133.9, 135.9, 136.6, 137.1, 191.3, 191.3. MS (EI): m/z 234 [M]+. HRMS (EI): calcd for C16H10O2 [M]+: 234.0681, found 234.0687. IR (KBr, cm-1): 3064, 2834, 2732, 2208, 1703, 1591, 1284, 1200.

Statistics shows that 696-41-3 is playing an increasingly important role. we look forward to future research findings about 3-Iodobenzaldehyde.

Reference:
Article; Wang, Liu-Gang; Zhan, Tian-Guang; Zhao, Xin; Jiang, Xi-Kui; Li, Zhan-Ting; Tetrahedron; vol. 68; 26; (2012); p. 5303 – 5310;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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 71838-16-9, 71838-16-9

The cadmium reagent was generated as in Example 1 using Cd metal (8.5 g, 0.075 mole), diethyl bromodifluoromethylphosphonate (18 g, 0.068 mole) and AcOH (1.0 niL) in DMF (80 mL). A 40 mL aliquot of this solution was added to CuCl (6.72 g, 0.068 mole) followed after 2 minutes by the addition of 3-bromo-4-iodotoluene (5.0 g, 0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with additional ether (300 mL) and the combined ether layer was washed with saturated ammonium chloride (500 mL) and water (500 mL) then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/ hexanes afforded 4.4 g of (2-bromo-4-methyl-phenyl)difluoromethylphosphonic acid diethyl ester. To the diethyl ester material obtained, (1.8 g, 0.005 mole) in carbon tetrachloride (CCl4, 30 mL), were added AIBN (0.033 g, 0.0002 mole) and N- bromosuccinimide (NBS, 0.89 g, 0.005 mole). The reaction was heated at reflux for 2 hours (a thin white suspension formed). The reaction was allowed to reach room temperature and the solvent was removed under vacuum. The residue was taken up in ethyl acetate (EtOAc, 120 mL) and washed with saturated NaHCtheta3 (60 mL) and brine (60 mL) then dried over MgSO4. Filtration and solvent evaporation afforded 2.1 g of crude product. Flash chromatography on silica gel using 20-30% ethyl acetate/hexanes afforded 1.11 g of (2- bromo-4-bromomethyl-phenyl)-difluoro-methylphosphonic acid diethyl ester.; Example 25 – Synthesis of Compound 25(2-Bromo-4-methylphenyl) difluoromethylphosphonic acid diethyl ester 25 To a suspension of 8.5 g Cd metal (0.075 mole), in 80 mL DMF (dried over 4A molecular sieves for 24 hours) was added 18 g of diethyl bromodifluoro-methylphosphonate (0.068 mole) and 1 mL glacial acetic acid. Within 4 minutes an exotherm started and lasted EPO ? for 20 minutes. The suspension was stirred for 3 hours and allowed to stand at room temperature for 30-40 minutes. A 40 mL aliquot of this solution was added to 6.72 g of CuCl (0.068 mole) followed after 2 minutes by the addition of 5 g of 3-bromo-4-iodotoluene (0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with 300 mL of ether and the combined ether layer was washed with 500 mL of saturated ammonium chloride and 500 mL of water, then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/hexanes afforded 4.4 g of Compound 25.

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, 2-Bromo-1-iodo-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CEPTYR, INC.; WO2006/55525; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com