Category: iodides-buliding-blocks

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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Iodo-3-(trifluoromethyl)benzene

General procedure: A flask was charged with i-PrMgCl·LiCl (4.63 mL, 1.0807 M) cooled to-20 C, and then neat iodobenzene (1.020 g, 5 mmol) was added. The reaction mixture was stirred for 30 min, and then, a ZnCl2 solution inTHF (5.5 mL, 1 M) was added. The mixture was stirred for 15 min and allowed to warm to r.t. over 30 min. A flask charged with 3e (242 mg, 1 mmol), Pd(dba)2 (30 mg, 5 mol%),and SPhos (40 mg, 10 mol%) was evacuated and back-filled with argon,and then, THF (1.5 mL) was added, and the reaction mixture wasstirred for 5 min. Next, the organozinc reagent PhZnCl (2.10 mL,0.5226 M) was added, and the mixture was stirred for 30 min. Themixture was quenched with aq NH4Cl (0.5 mL), diluted with Et2O (30mL), and the organic layer was washed with sat. aq NH4Cl (2 × 30 mL)and brine (30 mL). The organic layer was dried (MgSO4) and evaporated,and the residue was purified by column chromatography (eluent:CH2Cl2).

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; Dubovik, Julia; Bredihhin, Aleksei; Synthesis; vol. 47; 4; (2015); p. 538 – 548;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 104539-21-1, A common heterocyclic compound, 104539-21-1, name is 1-Iodo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11IO2, 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.

STR45 77 mg (0.158 mmol) of Compound 28 synthesised in Example 23 was dissolved in 2 ml of anhydrous DMF. To this solution, 255 mg (1.11 mmol) of 1-iodo-2-(2-methoxyethoxy)ethane and then 109 mg (0.79 mmol) of potassium carbonate were added. This reaction mixture was stirred in an atmosphere of argon at room temperature for 5 hours. The reaction mixture was then added to water. The mixture was then extracted with ethyl acetate. The extract layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated. The residue was chromatographed on silica gel and eluted with a mixed solvent of ethyl acetate and hexane (2:1), whereby ethyl (E)-7-[6-(4′-fluorophenyl)-2,3-dihydro -7-[2-(2-methoxyethoxy) ethoxy ]-2,2-dimethyl -4-(propan-2-yl)benzo[b]furan-5-yl ]-3,5-dihydroxy-6-heptenoate (Compound 30) was obtained in a yield of 70 mg (75.3%). Melting point: 97.5~98.5 C. (colorless, fine particle-shaped crystals, recrystallized from a mixed solvent of ethyl acetate and hexane) 1 H-NMR (300MHz, CDCl3) delta 1.21 (d, J=7. 1Hz, 3H), 1.22 (d, J=7.1Hz, 3H), 1.28 (t, J=7.2Hz, 3H), 1.10-1.44 (m, 2H), 1.50 (s, 6H), 2.32-2.46 (m, 2H), 2.64-2.68 (m, 1H), 3.13 (s, 2H), 3.27 (hept, J=7.1Hz, 1H), 3.34 (s, 3H), 3.38 (s, 4H), 3.45-3.50 (m, 2H), 3.55-3.60 (m, 1H), 3.94-3.99 (m, 2H), 3.99-4.10 (m, 1H), 4.18 (q, J=7.2Hz, 2H), 4.20-4.31 (m, 1H), 5.09 (dd, J=16.0 and 6.6Hz, 1H), 6.33 (dd, J=16.0 and 1.0Hz, 1H), 6.94-7.04 (m, 2H), 7.08-7.16 (m, 2H)ppm. IR (KBr): 3432, 2972, 2936, 2880, 1722, 1596 cm-1. Mass (m/z, %): 588 (M+, 100), 570 (76), 454 (23), 413 (17), 311 (17), 269 (11), 103 (36), 59 (40).

The synthetic route of 104539-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujirebio Inc.; US5523460; (1996); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 2265-91-0, 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 2265-91-0 as follows.

Step 1: tert-Butyl 4-(3,5-difluorophenyl) piperazine-1-carboxylate A solution of tert-butyl-piperazine-1-carboxylate (1.024 g, 5.5 mmol), 1,3-difluoro-5-iodobenzene (1.58 g, 6.6 mmol), t-BuONa (790 mg, 8.25 mmol), BINAP (137 mg, 0.22 mmol), Pd2(dba)3 (100 mg, 0.11 mmol) in dry toluene (40 mL) was stirred under N2 at 80 C. for 16 hrs. The reaction mixture was concentrated and the residue was purified by chromatography (silica, EtOAc/PE=1/10) to afford 1-(3,5-difluorophenyl)piperazine (1.5 g, 5.03 mmol, 91%) as a yellow oil. ESI-MS (EI+, m/z): 243.2 [M-55]+.

According to the analysis of related databases, 2265-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (136 pag.)US2019/389843; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 3930-83-4, 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. 3930-83-4, name is 2-Iodobenzamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a 10 mL reaction tube were added MCM-41-L-Proline-CuBr(135 mg, 0.1 mmol), 2-halobenzamide 1 (1.0 mmol), benzylamine derivative 2 (2.0 mmol), K2CO3 (3.0 mmol), and DMSO (3 mL). The reaction mixture was stirred at 110 or 120 C under air for 6-12 h.After being cooled to room temperature, the reaction mixture was diluted with 20 mL of EtOAc, and filtered. The MCM-41-L-Proline-CuBr complex was washed with distilled water (2 5 mL) and ethanol (2 5 mL), and reused in the next run. The filtrate was washed with water (2 10 mL) and dried over MgSO4. After being concentrated in vacuo, the residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc 3:1 to 2:1)to afford the target product 3.

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

Reference:
Article; Yan, Nan; You, Chongren; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 897; (2019); p. 161 – 169;,
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. 170112-66-0, name is 3,4,5-Trifluoroiodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 170112-66-0

General procedure: A Schlenk tube was dried using heat gun under reduced pressure and filled with argon. The tube was charged with TPPO (69.5mg, 0.25mmol) and then the tube was evacuated and refilled with argon (×3). To the tube were added THF (1mL), Me2Zn (0.6mL, 0.6mmol, 1.0M solution in hexane), and fluoroarene 1 (0.75mmol) at room temperature and then the tube was immersed in an oil bath. The reaction mixture was gradually warmed to 75C and stirred for 3h. The mixture was cooled to room temperature and allylic bromide (0.5mmol) was added. The resultant mixture was warmed to 75C and stirred for 16h. The reaction mixture was quenched with saturated aqNH4Cl solution followed by extraction with Et2O (×3). Combined organic layer was washed with brine (×1), dried over Na2SO4, and filtered. Volatiles were removed under reduced pressure and the residue was purified by flash column chromatography on silica gel to afford analytically pure product.

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 170112-66-0.

Reference:
Article; Kurauchi, Daisuke; Hirano, Keiichi; Kato, Hisano; Saito, Tatsuo; Miyamoto, Kazunori; Uchiyama, Masanobu; Tetrahedron; vol. 71; 35; (2015); p. 5849 – 5857;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 19821-80-8, A common heterocyclic compound, 19821-80-8, name is 1,3-Dibromo-2-iodobenzene, molecular formula is C6H3Br2I, 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.

2,6-dibromoiodobenzene (1.0 g, 2.8 mmol), 1-naphthaleneboronic acid (0.48 g, 2.8 mmol),Tetrakis(triphenylphosphine)palladium (0.33 g, 0.28 mmol), lithium hydroxidemonohydrate (0.46 g, 11 mmol) were charged into a flask, and purged 3 times with nitrogen,the degassed acetonitrile (100 mL) and degassed water (10 mL) were added, and stirred at 70C for 14 hunder nitrogen atmosphere. The reaction mixture was cooled to room temperature and diluted with EtOAcand H2O, then separated and the organic layer was dried over Na2SO4 and concentrated under reducedpressure. The residue was purified by column chromatography on silica gel to give the desired product(0.69 g, 69%). 1H NMR (500 MHz, CDCl3): 7.95-7.91(m, 2H), 7.71 (d, J = 8.0 Hz, 2H), 7.58 (t, J = 8.0Hz, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.43 (t, J = 8.0 Hz, 1H), 7.34-7.30 (m, 2H), 7.18 (t, J = 8.0 Hz, 2H);13C NMR (125 MHz, CDCl3) 141.5, 138.9, 133.5, 131.9, 130.9, 130.2, 128.6, 128.5, 127.0, 126.5, 126.1,125.5, 125.4, 124.9; HRMS (EI-TOF): Calcd for C16H10Br2, 359.9149; found 359.9152.

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; Zhou, Haifeng; Uozumi, Yasuhiro; Synlett; vol. 24; 19; (2013); p. 2550 – 2554;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 626-01-7,Some common heterocyclic compound, 626-01-7, name is 3-Iodoaniline, molecular formula is C6H6IN, 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 round bottom flask was charged with 28 4-iodoaniline (5, 3g, 13.7mmol, 1.0 eqv.) and 29 water (15.2mL, 0.90M). 30 Concentrated HCl (2.5mL 2.1 eqv.) was added to vigorously stirred reaction mixture in an ice-water bath. A pre-cooled solution of 31 NaNO2 (0.95g, 13.7mmol, 1.0 eqv.) in water (5.50mL, 2.50M) was added dropwise to the reaction mixture, after which time the reaction mixture was stirred for 15min. The solution of 32 NaN3 (0.89g, 13.7mmol, 1.0 eqv.) in water (5.50mL 2.50M) was added dropwise to the reaction mixture while maintaining the temperature in the ice bath, and then the reaction mixture was stirred an additional 20min at 0C, then stirred at rt for another 3h. The reaction mixture was extracted with EtOAc (2×50mL) and the aqueous layer was adjusted to pH 8-10 with NaHCO3 before discarding. The combined organic solution was washed with water and brine and dried over Na2SO4, filtered and concentrated under reduced pressure. The crude azidoiodobenze derivative was further purified by flash column chromatography over silica gel with 0-5% ethylacetate/hexanes as eluent to afford 33 4-azidoiodobenze (7, 2.60g, 78%). 1H NMR (400MHz, CDCl3) delta 7.63 (d, J=8.7Hz, 2H), 6.77 (d, J=8.7Hz, 2H). 13C NMR (101MHz, CDCl3) delta 140.06, 138.79, 121.14, 88.31.

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

Reference:
Article; Hayes, Karen E.; Batsomboon, Paratchata; Chen, Wei-Chih; Johnson, Brennan D.; Becker, Andreas; Eschrich, Steven; Yang, Yan; Robart, Aaron R.; Dudley, Gregory B.; Geldenhuys, Werner J.; Hazlehurst, Lori A.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1479 – 1488;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 450412-28-9, 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. 450412-28-9, name is 1-Bromo-3-chloro-2-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-bromo-3-chloro-2-iodobenzene 200.00 g (1.0 eq),2-aminophenol 68.77 g (1.0 eq), K3PO4 267.55 g (2.0 eq),1.61 g (0.005 eq) of Pd (t-Bu3P) 2 was dissolved in 1.5 L of toluene, refluxed and stirred.The solution was concentrated under reduced pressure for 3 hours.After that, it was completely dissolved in CHCl3, washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 137.35 g (yield 73%) of a compound represented by the formula 7-a.

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, 1-Bromo-3-chloro-2-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG Chem, Ltd.; Kim Min-jun; Park Tae-yun; Cho Seong-mi; Lee Jeong-ha; (88 pag.)KR2017/113319; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 4897-68-1,Some common heterocyclic compound, 4897-68-1, name is 1-Bromo-2-iodo-4-methoxybenzene, molecular formula is C7H6BrIO, 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.

The 135mg (1mmol) benzothiazole, 376mg (1.2mmol) 1- bromo-2-iodo-4-methoxybenzene, 2.5mg (0.01mmol) CuSO4·5H2O, 19.4mg (0.1mmol) ligand L4,240mg (6mmol) NaOH, 2gPEG-600, was added 10mL reaction tube, sealed, under the reaction condition of 80 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, purified by silica gel column chromatography separation and purification, to give 3-methoxy-phenothiazine 172mg, yield 75%.

The synthetic route of 4897-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Wan, Yiqian; Huang, Manna; Huang, Dongting; Zhu, Xinhai; (11 pag.)CN104529938; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 82998-57-0, 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. 82998-57-0 name is 3-Iodo-4-methylbenzoic acid, 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.

Add 2 drops of DMF into 628 mg 3-iodo-4-methylbenzoic acid (2.2 mmol) in 20 mL SOCl2 and reflux for 2 h. After vacuum evaporation of SOCl2, add 6.0 mL anhydrous THF and get the pale yellow solution. Dissolve the product from step 1, 524 mg 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine (2.0 mmol) in 6.0 mL anhydrous THF and add 10 mmol Et3N, and the pale yellow solution prepared previously is added drop wise till it is all added. The reaction mixture rises to room temperature for 1 hr. The reaction was quenched with addition of brine and extracted with EtOAc. The combined extraction organic layers was dried and concentrated under vacuum, the residue was purified through column chromatography to afford 873 mg desired product. (90%) MS (ESI), m/z: 486 (M++H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-4-methylbenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Guangzzhou Institute of Biomedicine and Health, Chineses Academy of Sciences; Ding, Ke; Wang, Deping; Pei, Duanqing; Zhang, Zhang; Shen, Mengjie; Luo, Kun; Feng, Yubing; US2013/196985; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com