Author: Jessica.F

Synthetic Route of 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: Polymer supported Cu(II) catalyst (0.05 g, 0.0098 mmol) in DMSO (5 mL) was taken in a 100 ml R.B flask and stirred at room temperature for 10 min. Then aryl halide (1 mmol), phenol(1 mmol), tetrabutylammonium bromide (tBu4NBr) (0.1 mmol),Cs2CO3 (1 mmol) and DMSO (5 mL) were added to it. The final reaction mixture was refluxed at 120 C under an open air condition.The reaction mixtures were collected at different time intervals and identified by GCMS and quantified by GC. After the completion of the reaction, the catalyst was filtered off and washed with water followed by acetone and dried in oven. The filtrate was extracted with ethyl acetate (3 x 20 ml) and the combined organic layers were dried with anhydrous Na2SO4 by vacuum. The filtrate was concentrated by vacuum and the resulting residue was purified by column chromatography on silica gel to provide the desired product.

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; Islam, Sk.Manirul; Mondal, Sanchita; Mondal, Paramita; Roy, Anupam Singha; Tuhina; Salam, Noor; Mobarak, Manir; Journal of Organometallic Chemistry; vol. 696; 26; (2012); p. 4264 – 4274;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 144550-76-5, These common heterocyclic compound, 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, 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.

c. Methyl 2-amino-6-ethylbenzoate To a stirred mixture of zinc chloride (8.6 g, 63 mM, previously dried at 200 C. for 2 hr under high vacuum) in tetrahydrofuran (105 mL) under a nitrogen atmosphere was added dropwise a solution of ethyl magnesium chloride (63 mM) in diethyl ether (31.5 mL). After the addition was completed, dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (0.107 g, 0.126 mM) was added to the resulting stirred thick white mixture followed by the dropwise addition of methyl 2-amino-4-iodobenzoate (3.5 g, 12.6 mM) in tetrahydrofuran (15 mL). The resulting reaction mixture was stirred at room temperature for 2.5 hr and then poured slowly into water (300 mL). The water mixture was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated. The residue was chromatographed over silical gel (eluant: Hexanes/diethyl ether; 8.5/1.5) to provide the title ester (1.0 g, 43.5%) as a pale yellow oil; MS(CI): 180 (M+H). 250-MHz 1 H NMR (DMSO-d6); 7.04 (t, J=7.8, 1H), 6.53 (d, J=8.2, 1H), 6.42 (d, J=7.1, 1H), 5.55 (s, 2H, exchangeable), 3.80 (s, 3H), 2.59 (q, J=7.5, 1H), 1.08 (t, J=7.5, 3H).

Statistics shows that Methyl 2-amino-4-iodobenzoate is playing an increasingly important role. we look forward to future research findings about 144550-76-5.

Reference:
Patent; Imperial Chemical Industries, PLC; US5599814; (1997); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 624-76-0, 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. 624-76-0, name is 2-Iodoethanol, This compound has unique chemical properties. The synthetic route is as follows.

Step C (1,1 -dimethylethyl)(2-iodoethoxy)dimethylsilane .OTBDMS Iodoethanol (2.68 kg, 15.4 mol), CH2CI2 (12 L) and imidizaole (1.556 kg, 22.63 mol) were chilled in an ice bath. A solution of t-butyldimethylchlorosilane (2.536 kg, 16.32 mol) in CH2CI2 (2.5 L) was added to the reaction over a 2 h period. The resulting white suspension was allowed to warm to rt over an 18 h. The reaction was worked up by washing with water and brine). The organic layer was dried (MgSC^) and evaporated under reduced pressure to provide the product of Step C as a light yellow oil. FontWeight=”Bold” FontSize=”10″ H NMR (400MHz, CDC13) delta = 3.75 (t, J = 7.0 Hz, 2 H), 3.11 (t, J = 7.0 Hz, 2 H), 0.77 – 0.89 (m, 10 H), 0.00 (s, 6 H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WINTERS, Michael P.; BRANUM, Shawn; FAWZY, Nagy E.; KANG, Fu-An; REUMAN, Michael; RUSSELL, Ronald K.; SUI, Zhihua; TELEHA, Christopher A.; WO2013/152269; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 31599-61-8, name is 4-Iodo-1,2-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 31599-61-8, Application In Synthesis of 4-Iodo-1,2-dimethylbenzene

General procedure: CAUTION: Azides are potentially explosive and so appropriateprecautions against blast must be taken when preparing, handlingand heating them. Reactions must be carried out on a small scale. A mixture of the aryl iodide (1.0 mmol), sodium azide (1.2 mmol),DBU (0.15 mmol) and Cu(OAc)2·H2O (0.1 mmol) in DMSO (3.0 mL)in a 10 mL flask was heated to 95 C (the temperature in the reaction flask was monitored) for 1.5-5.0 h. After the reaction was completed asjudged by TLC, the cooled mixture was poured into water (30 mL)containing several drops of ammonia. The resulting aqueous phase was extracted with ethyl acetate (3 × 30 mL). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was loaded on asilica gel column and eluted with petroleum ether (boiling range 60-90 C)/ethyl acetate to afford the product.

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:
Article; Jiang, Yuqin; Suo, Huajun; Zhao, Yaru; Li, Xiyong; Sun, Yamin; Li, Xingfeng; Dong, Wenpei; Li, Wei; Zhang, Weiwei; Xu, Guiqing; Journal of Chemical Research; vol. 42; 5; (2018); p. 247 – 250;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25245-27-6,Some common heterocyclic compound, 25245-27-6, name is 1-Iodo-3,5-dimethoxybenzene, molecular formula is C8H9IO2, 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: A mixture of the styrene (3 mmol), the halogenated benzene (3 mmol), triethanolamine (3 mmol) and Pd(II) acetate (0.03 g) was stirred under argon at 100 C for 24 h. The reaction was cooled to 25 C, quenched by the addition of dil. aq. hydrochloric acid (2 N, 10 ml), and extracted with ether (3 × 100 ml). The organic phases were dried (Na2SO4), the solvents evaporated, and the crude product subjected to chromatography (silica gel, hexane/ethyl acetate mixtures).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-3,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Albert, Sabrina; Horbach, Ralf; Deising, Holger B.; Siewert, Bianka; Csuk, Rene; Bioorganic and Medicinal Chemistry; vol. 19; 17; (2011); p. 5155 – 5166;,
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. 364-11-4, name is 1-Bromo-4-iodo-2-(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 364-11-4

General procedure: To a 20 mL vial with a stir bar was added aryl halide 1 (2.00 mmol), Pd(dba)2 (28.8 mg, 2.5 mol %), Xantphos (28.9 mg, 2.5 mol %). The vial was sealed with a Teflon-lined cap and THF (6.0 mL) was added. The mixture was vacuumed and backfilled with nitrogen (3×). A solution of ethyl 2-bromozincacetate (2a) in THF (0.40 M, 6.0 mL, 1.2 equiv) filtered through a Target Nylon 0.45 mum filter (1.25-inch OD) was syringed in and the reaction mixture was then heated to 65 C and monitored by HPLC. Upon reaction completion based on HPLC analysis (?95% conversion unless the reaction was stalled), the mixture was cooled to room temperature and quenched with 1 M aq HCl (5.0 mL), followed by addition of brine (5.0 mL). The organic layer was separated and concentrated in vacuum. The residue was purified by silica gel column chromatography using gradient EtOAc in hexanes.

The synthetic route of 364-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wong, Brian; Linghu, Xin; Crawford, James J.; Drobnick, Joy; Lee, Wendy; Zhang, Haiming; Tetrahedron; vol. 70; 7; (2014); p. 1508 – 1515;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 75581-11-2, A common heterocyclic compound, 75581-11-2, name is 4-Iodo-1-methoxy-2-methylbenzene, molecular formula is C8H9IO, 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 typical reaction, styrene (1.0 mmol) and aryl halide (1.5 mmol) were reacted in a homogeneous mixture of toluene and PEG-600 (20 ml, 3:1) in the presence of 3 mol % of Cl2PdPEGD catalyst(34.4 mg) and Cs2CO3 (1.5 mmol), under a nitrogen atmosphere at 80 C for 5 h until complete consumption of aryl halide. The reaction progress was monitored by TLC and GC analysis. The mixture was cooled to room temperature and 20 ml of n-hexane was added to separate lower catalyst-philic PEG phase from upper product phase. The product was isolated by decantation and evaporation of solvents under vacuum. Catalyst-philic PEG phase containing polyether palladium catalyst was subjected to reuse by charging with the same amount of the substrates styrene (1.0 mmol) and aryl halide (1.5 mmol), Cs2CO3 (2.0 mmol) and toluene. The identity and purity of the products were confirmed by GC and GC-MS.

The synthetic route of 75581-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sawant, Dinesh; Wagh, Yogesh; Bhatte, Kushal; Panda, Anil; Bhanage, Bhalchandra; Tetrahedron Letters; vol. 52; 18; (2011); p. 2390 – 2393;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

98-61-3, name is 4-Iodobenzenesulfonyl chloride, 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

11 (135 mg, 0.50 mmol), Na2B4O7 (1.00 g, 4.97 mmol) and 4-iodobenzenesulfonyl chloride (151 mg, 0.50 mmol) were suspended in H2O (30 mL) under vigorous stirring. The reaction mixture was stirred at rt overnight meanwhile a colorless precipitate was formed. This solid was dissolved by addition of 1 M NaOH and the resulting solution was extracted with CH2Cl2 to remove byproducts. The aqueous layer was treated with conc. HCl to adjust pH value to 1 and the formed precipitate was filtered, washed with H2O and dissolved in THF. Removal of the solvent under reduced pressure gave 5l. Colorless solid, mp 238 C (dec.), yield 162 mg (61 %). C21H18IN3O4S (535.4). Rf = 0.82 (ethyl acetate, detection: 254 nm). 1H NMR (400 MHz, DMSO-D6): delta [ppm] = 4.07 (d, J = 6.3 Hz, 2H, NHCH2), 7.39 (d, J = 7.9 Hz, 2H, 2-HB, 6-HB), 7.52 (t, J = 7.5 Hz, 2H, 3-HC, 5-HC), 7.57-7.63 (m, 3H, 2-HA, 6-HA, 4-HC), 7.86 (d, J = 8.0 Hz, 2H, 3-HB, 5-HB), 7.93 (d, J = 7.3 Hz, 2H, 2-HC, 6-HC), 7.99 (d, J = 8.3 Hz, 2H, 3-HA, 5-HA), 8.34 (t, J = 6.3 Hz, 1H, SO2NHCH2), 10.47 (s, 1H, ArBCONHNH), 10.48 (s, 1H, NHNHCOArC). 13C NMR (101 MHz, DMSO-D6): delta [ppm] = 45.7 (1C, NHCH2), 100.5 (1C, C-4A), 127.4 (2C, C-2C, C-6C), 127.47 (2C, C-3B, C-5B), 127.49 (2C, C-2B, C-6B), 128.3 (2C, C-2A, C-6A), 128.5 (2C, C-3C, C-5C), 131.4 (1C, C-4B), 131.8 (1C, C-4C), 132.6 (1C, C-1C), 138.1 (2C, C-3A, C-5A), 140.2 (1C, C-1A), 141.6 (1C, C-1B), 165.5 (1C, ArBCONHNH), 165.8 (1C, NHNHCOArC). FT-IR: nu [cm-1] = 3410, 3318 (N-H), 3152, 3075 (C-HAr), 2870 (C-Haliph.), 1701, 1659 (C=O), 1612, 1566, 1516 (C=CAr), 1315, 1153 (SO2), 1057 (Ar-I), 818, 729, 702 (Ar-Hout of plane). HRMS (APCI): m/z = 535.0137 (calcd. 536.0135 for C21H19IN3O4S [M+H]+). HPLC: tR = 19.1 min, purity 98.1 %.

The synthetic route of 98-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mueller, Sebastian L.; Schreiber, Julian A.; Schepmann, Dirk; Strutz-Seebohm, Nathalie; Seebohm, Guiscard; Wuensch, Bernhard; European Journal of Medicinal Chemistry; vol. 129; (2017); p. 124 – 134;,
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. 6940-76-7, name is 1-Chloro-3-iodopropane, A new synthetic method of this compound is introduced below., Computed Properties of C3H6ClI

Step B: To a solution of 3,4-difluorobenzenesulfinic acid (2.5 g, 14.0 mmol) in dimethyl formamide (20 mL) was added 1-chloro-3-iodopropane (4.46 mL, 42.1 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.82 mL, 15.4 mmol) and the reaction was stirred overnight at ambient temperature. The reaction was poured into water and extracted into diethyl ether. The combined organic layers were washed with water, brine, dried over MgS04, filtered and concentrated in vacuo. The material was purified over silica gel (4: 1 hexanes/EtOAc) to yield 4-(3-chloropropylsulfonyl)-1,2-difluorobenzene (2.8 g, 80%).

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; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENSCIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John Peter; HINKLIN, Ronald Jay; PRATT, Scott; SINGH, Ajay; TURNER, Timothy M.; WO2013/66869; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 116632-39-4, name is 5-Bromo-2-iodotoluene, 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 116632-39-4, HPLC of Formula: C7H6BrI

sec-BuLi (1.4M in cyclohexane, 137.4 ml, 192.4mmol) was added dropwise to a suspension of (2,8-dibenzothiophenediyl)bis-9H,9’H-carbazole (82.5 g, 160.3 mmol)in tetrahydrofuran (1650 ml) at -74 C. After stirring at -40C. for 4 hours, the reaction mixture was re-cooled to -74 o C.and isopropoxyboronic acid, pinacol ester ( 45.8 ml, 224.4mmol) was added dropwise and the mixture allowed towarm to room temperature over night. It was then cooled to-30 C., quenched by the dropwise addition of HCl (2M indiethylether, 88.2 ml, 176.3 mmol), warmed to ambienttemperature and concentrated under reduced pressure. Theresulting precipitate was removed and the filtrate concentratedunder reduced pressure and recrystallized (once fromhexane:toluene and twice from acetonitrile:toluene) to give(A) as a white solid (49.6 g, 48% yield) after drying at 50C. under vacuumHPLC: 95.88%.[0126] 1H-NMR (600 MHz, CDC13 ):delta H [ppm] 1.47 (s,12H), 7.28 (m, 4H), 7.40 (m, 8H), 7.70 (dd, 1=1.9 Hz, 8.5Hz, lH), 8.15 (m, 6H), 8.29 (d, 1=1.7 Hz, lH), 8.38 (d, 1=2.0Hz, lH).

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; Cambridge Display Technology Limited; Sumitomo Chemical Company Limited; Steudel, Annette; Bourcet, Florence; (29 pag.)US2018/342684; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com