Month: October 2020

2401-21-0, name is 1,2-Dichloro-3-iodobenzene, 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. 2401-21-0

EXAMPLE 48 Benzyl 3-chloro-trans-6-(1-hydroxyethyl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]heptane-2-carboxylate STR90 The 2:1 mixture of diastereoisomers of benzyl trans-6-(1-hydroxyethyl)-7-oxo-3-phenylthio-1-azabicyclo[3.2.0]heptane-2alpha-carboxylate (99) and (100) (0.047 g) was dissolved in chloroform (4 ml) and stirred in an ice bath under argon. It was treated with water (0.005 g), pyridine (0.038 g) and then iodobenzene dichloride (0.097 g). After a period of 2 hours the solution was concentrated and applied to a column of silica gel 60 (<230 mesh). Elution with ethyl acetate/60¡ã-80¡ã petroleum ether 7:3 gave benzyl 3-chloro-trans-6-(1-hydroxyethyl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]heptane-2-carboxylate (81) (0.015 g); m.p. 154¡ã-159¡ã (chloroform/60¡ã-80¡ã petroleum ether); numax (CHCl3) 3480, 2980, 1780, and 1745 cm-1; tau(CDCl3) 2.3-2.9 (10H, m, phenyls), 4.75 (H, s, benzyl CH2), 4.95 (1H, s, C2-H), 5.7-6.1 (2H, m, C5-H and C8-H), 6.58 (1H, dd J5 and 3 Hz, C6-H), 7.08 (1H, dd J 15 and 9 Hz, C4-H), 8.13 (1H, brs, OH), 8.23 (1H, brd J 15 Hz, C4-H) and 8.72 (3H, d J 6 Hz, CH3); (Found: C, 58.9; H, 4.7; N, 3.2percent. C22 H22 ClNO5 S requires C, 59.0; H, 5.0 and N, 3.1percent). Statistics shows that 2401-21-0 is playing an increasingly important role. we look forward to future research findings about 1,2-Dichloro-3-iodobenzene. Reference:
Patent; Beecham Group Limited; US4223038; (1980); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

628-21-7, Adding a certain compound to certain chemical reactions, such as: 628-21-7, name is 1,4-Diiodobutane, 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 628-21-7.

Into a 100 ml flask to which a condensing device was connected, 50 ml of acetonitrile, 15.5 g (0.05 mol) of 1,4-diiodobutane and 6.8 g of aqueous ammonia (NH3 0.1 mol) were added. 20C constant temperature stirring reaction 12h. The obtained reaction solution was subjected to cation chromatography. According to the product content in the reaction solution. The yield was calculated to be 85.35%.

According to the analysis of related databases, 628-21-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changshu Institute Co., Ltd., East China University of Science and Technology; East China University of Science and Technology; Guan, Shiyou; Feng, Lei; Xiong, Yachao; Yan, Xinzhu; (16 pag.)CN105732645; (2016); A;,
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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., 3032-81-3

To an oven dried 8 mL vial with teflon cap purged with N2 was added Zinc dust (298 mg, 4.56 mmol), DMF(1.5 mL), and iodine (57.8 mg, 0.228 mmol). To this mixture was added (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (500 mg, 1.519 mmol), immediately followed by iodine (57.8 mg, 0.228 mmol).Pd2(dba)3 (69.6 mg, 0.076 mmol), 2-DICYCLOHEXYLPHOSPHINO-2?,6?-DIMETHOXYBIPHENYL(62.4 mg, 0.152 mmol), 1,3-dichloro-5-iodobenzene (622 mg, 2.279 mmol) and the reaction mixture wasallowed to stir at rt for 16 h. The crude mixture was diluted in EtOAc (30 mL) and DMF was removed withfour aqueous washes. The organic phase was dried over anhydrous sodium sulfate. The solution was filteredand concentrated, and the crude was purified by silica gel chromatography using 100percent hexanes to 30percentEtOAc/Hexanes. The desired product was obtained as a pale yellow oil, (S)-methyl 2-((tertbutoxycarbonyl)amino)-3-(3,5-dichlorophenyl)propanoate, 0.160 g yield in 77percent purity by LCMS analysis.Analysis LCMS condition F: Retention time=2.84 min; ESI-MS(+) m/z 348.1 (M+H).

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; Bristol-Myers Squibb Company; Miller, Michael Matthew; Mapelli, Claudio; Allen, Martin Patrick; Bowsher, Michael S.; Boy, Kenneth M.; Gillis, Eric P.; Langley, David R.; Mull, Eric; Poirier, Maude A.; Sanghvi, Nishith; Sun, Li-Qiang; Tenney, Daniel J.; Yeung, Kap-Sun; Zhu, Juliang; Reid, Patrick C.; Scola, Paul Michael; (892 pag.)US9308236; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

608-28-6, Adding a certain compound to certain chemical reactions, such as: 608-28-6, name is 2-Iodo-1,3-dimethylbenzene, 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 608-28-6.

2,2′,6-trimethyl-1,1′-biphenyl (89): To a mixture of Ni-Cat.(0.0125 mmol Nil2+0.025 mmol VIa) and Ar-I 87 (0.036mL, 0.058 g, 0.25 mmol) 1.0 mL of CPME was added. Themixture was stirred for 10 mins. Then the water (0.02 mL,0.02 g, 1.11 mmol) was added. To the mixture, boronic acid88 (0.068 g, 0.5 mmol), bases (0.160 g, 0.75 mmol) wereadded. The reaction mixture was stirred at 105 C. (asmentioned) and aliquot was taken after different time intervalto analyze the data by GC/MS. After that the reactionmixture was filtered through neutral alumina, concentratedunder vacuum, purified by flash chromatography withhexane.1 H NMR (CDC13, 400 MHz): o1.99 (s, 6H), 2.01 (s,3H), 7.05-7.08 (m, lH), 7.14-7.35 (m, 6H); 13C NMR(CDC13, 100 MHz): o19.4, 20.3, 126.0, 126.9, 126.9, 127.2,128.8, 130.0, 135.6, 135.8, 140.5, 141.0.

According to the analysis of related databases, 608-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; Desrosiers, Jean-Nicolas; Fandrick, Daniel Robert; Haddad, Nizar; Li, Guisheng; Patel, Nitinchandra D.; Qu, Bo; Rodriguez, Sonia; Senanayake, Chris Hugh; Sieber, Joshua Daniel; Tan, Zhulin; Wang, Xiao-Jun; Yee, Nathan K.; Zhang, Li; Zhang, Yongda; (58 pag.)US2018/155375; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

628-21-7, 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. 628-21-7, name is 1,4-Diiodobutane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

n-Butyl lithium (2.5 M in hexanes, 4.2 mL, 0.5 mmol) was added dropwise to a suspension of indolinone (0.665 mg, 5 mmol) and TMEDA (1.5 mL, 10 mmol) in THF (20 mL) at -78C in a dried flask under nitrogen. After 1 hour at -78C, 1,4- diiodobutane (3.3 mL, 25 mmol) was added dropwise and the mixture was allowed to slowly warm to rt. After 12 hours at rt, saturated aqueous ammonium chloride was added to the mixture and this mixture was extracted with EtOAc. The combined organic phases were washed with water, brine, dried over magnesium sulphate, filtered and concentrated in vacuo. Chromatography on silica (10-30% EtOAc in isohexane) gave isolation of the desired compound as a pale pink solid (393 mg, 2.1 mmol, 42%). ? NMR (400 MHz): delta 1.90 (m, 2H), 2.03 (m, 2H), 2.10 ( m, 2H), 2.21 (m, 2H), 6.94 ( m, 1H), 7.04 ( m, 1H), 7.20 (m, 2H), 8.75 ( bs, 1H). LC/MS 188 (MH+).

The synthetic route of 1,4-Diiodobutane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RE:VIRAL LTD; COCKERILL, Stuart; PILKINGTON, Christopher; LUMLEY, James; ANGELL, Richard; MATHEWS, Neil; WO2013/68769; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3058-39-7, 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. 3058-39-7 name is 4-Iodobenzonitrile, 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: To a screw-capped vial (4-mL) were added Cs2CO3 (1.0 mmol, 325 mg), Cu2O (0.005 mmol, 0.7 mg), 1H-imidazole-4-carboxylic acid (0.01 mmol, 1.1 mg) and acetonitrile (0.25 mL). The vial was sealed with septum and allowed to stir for a while; the iodoarene (0.5 mmol) and phenol (0.6 mmol) were then injected into the reaction mixture via a syringe. The septum was removed, and the vial was sealed with a screw cap. The reaction mixture was stirred at 80 oC for 24 h. The crude reaction mixture was diluted with CH2Cl2, filtered through a thin Celite pad, and concentrated in vacuo. The residue was isolated through a column chromatography by using hexane and ethyl acetate as eluent to give the pure product. Products 3a-v were obtained according to this procedure. The known structures were characterized by the 1H NMR and 13C NMR of reported literatures.1-3 Spectral data, 1H NMR and 13C NMR spectra for all the new compounds are listed below.

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

Reference:
Article; Cheng, An-Yi; Hsieh, Jen-Chieh; Tetrahedron Letters; vol. 53; 1; (2012); p. 71 – 75;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

71838-16-9, These common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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.

[(2-Bromo-4-methyl-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester: A solution of (bromo-difluoro-methyl)-phosphonic acid diethyl ester (25.00 g, 93.6 mmol) in N,N-dimethylacetamide (50 mL) was added drop wise into a suspension of activated zinc (6.12 g, 93.6 mmol) under Argon. The reaction was initiated by heating and kept under 50 C. After the mixture was stirred for 3 h, copper (I) bromide (13.43 g, 93.6 mmol) was added and stirred for 1 h. A solution of 2-bromo-l-iodo-4-methyl-benzene (11.88 g, 40.0 mmol) in N,N-dimethylacetamide (25 mL) was added slowly to the reaction mixture. The resulting suspension was then stirred at room temp for 18 h. Water (100 mL) was added to the reaction mixture and the solution filtered through celite. The filtrate was diluted with EtOAc (250 mL) and organic layer was washed with H20 (50 mL), NaHC03 (5%, 50 mL) and H20 (50 mL). The solvent was removed and the residue was purified by column chromatography on silica gel, eluting with hexanes/EtOAc (4:1) to provide a colorless oil (11.75 g, 82%): .H NMR (300 MHz, CDC13) 8 7.51 (d, 1H), 7.49 (s, 1H), 7.19 (d, 1H), 4.26 (m, 4H), 2.36 (s, 3H), 1.48 (s, 9H), 1.37 (m, 6 H).

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 71838-16-9.

Reference:
Patent; CENGENT THERAPEUTICS, INC.; WO2006/28970; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

364-77-2, 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. 364-77-2, name is 2-Iodo-5-fluoronitrobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

STEP 1. Methyl trans-(4-fluoro-2-nitro)cinnamate The title compound was prepared according to the procedure described in step 1 of Example 24 from 3-fluoro-6-iodonitrobenzene and methyl acrylate. 1H-NMR (CDCl3) delta: 8.67 (1H, d, 15.8Hz), 7.78 (1H, dd, 8.07Hz, 2.65Hz), 7.68-7.63 (2H, m), 6.34 (1H, d, 15.8Hz), 3.84 (3H, s).

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

Reference:
Patent; PFIZER INC.; EP1065206; (2001); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 645-00-1, name is 1-Iodo-3-nitrobenzene, I believe this compound will play a more active role in future production and life. 645-00-1

General procedure: For example, synthesis of 1,2-diphenylethyne, 3a. To an oven-dried 5 mL microwave vessel was added Pd(PPh3)2Cl2 (3.5 mg, 0.005 mmol, 2 mol %) and CuI (1.9 mg, 0.01 mmol, 4 mol %). The vessel was then capped and purged with N2 before addition of Cyrene (0.5 mL, 0.5 M), Et3N (38 muL, 0.275 mmol, 1.1 equiv), iodobenzene (27.9 muL, 0.25 mmol, 1 equiv), and phenylacetylene (28.8 muL, 0.263 mmol, 1.05 equiv). The reaction mixture was heated to 30 C and maintained at this temperature with stirring for 1 h before the vessel was vented, and decapped. The solution was then diluted with EtOAc (10 mL), and washed with water (2¡Á 20 mL) and brine (2 ¡Á 20 mL). The organics were then passed through a hydrophobic frit and concentrated under reduced pressure to give a yellow oil, which was purified by flash chromatography (silica gel, 0-5% Et2O in petroleum ether) to afford the title compound as a white solid (44.5 mg, quant.).

The chemical industry reduces the impact on the environment during synthesis 645-00-1. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wilson, Kirsty L.; Kennedy, Alan R.; Murray, Jane; Greatrex, Ben; Jamieson, Craig; Watson, Allan J. B.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2005 – 2011;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19230-28-5, 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. 19230-28-5 name is 1,3-Dichloro-2-iodobenzene, 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.

Under an argon atmosphere,2- [3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) biphenyl-5-yl] -4,6- diphenyl- 1,3,5-triazine 2.0 g, 3.9 mmol),2,6-Dichloro-1-iodobenzene (1.2 g, 4.3 mmol),And bis (triphenylphosphine) palladium dichloride(55 mg, 78 mumol)Was suspended in THF (39 mL)To this was added 3 M potassium carbonate aqueous solution (2.6 mL).The mixture was stirred at 80 C. for 30 hours and then allowed to cool to room temperature. Water (30 mL) and methanol (30 mL) were added to the reaction solution, and the resulting precipitate was separated by filtration and washed with water, methanol and hexane.By recrystallizing the obtained solid from toluene,A white solid (1.3 g, 2.5 mmol, 64%) of the intermediate 2- (2 ‘, 6’-dichloro-5-phenylbiphenyl-3-yl) -4,6- diphenyl- ) Was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dichloro-2-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE; AIHARA, HIDENORI; SHONO, TOMOHIRO; UCHIDA, NAOKI; NOMURA, KEISUKE; HATTORI, KAZUKI; (90 pag.)JP2018/95562; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com