Tag: M.W=200-300

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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3032-81-3

Reference Example 3Synthesis of bis(3,5-dichlorophenyl)sulfideThe compound entitled was synthesized in accordance with the following scheme.Into a 300 ml three-necked glass flask equipped with a thermometer, a reflux condenser and a stirrer, 3,5-dichloroiodobenzene 22.6 g (82.8 mmol) and dimethylformamide 200 ml were added, and argon was passed through the solution for 2 hours and 15 minutes.Then, 3,5-dichlorothiophenol 14.8 g (82.6 mmol), potassium carbonate 22.8 g (165 mmol) and cuprous iodide 1.57 g (8.24 mmol) were added, which were reacted for 3 hours at 95 to 100¡ã C. with stirring.After completion of the reaction, the reaction mixture was cooled down to room temperature and separated with the addition of water and hexane:ethyl acetate (1:1), and the organic layer obtained was dried with anhydrous magnesium sulfate.After filtration, the filtrate was concentrated under reduced pressure, and the obtained concentrate was purified by recrystallization, simple silica-gel column chromatography (eluent; hexane) to obtain bis(3,5-dichlorophenyl)sulfide 25.4 g as white solid (isolation yield; 95percent).

The synthetic route of 3032-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE INDUSTRIES, LTD.; US2011/140044; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

108078-14-4, A common heterocyclic compound, 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, molecular formula is C8H7IO2, 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.

Example 87; 2-lodo-3-methylbenzoic acid (2.6 g, 10 mmol) was dissolved in THF (15 mL), followed by slow addition of 1 M lithium aluminium hydride in THF (10 mL, 10 mmol). The colorless solution turned into light yellow. Upon the completion of addition, the reaction was stirred at ambient temperature for 30 min then quenched with water (50 mL). Ethyl acetate ( 25 EPO mL) was added to the reaction mixture which was filtered and transferred to a separation funnel. The two layers were separated and the water layer was further extracted with ethyl acetate (2 x 100 ml_). The combined organic layer was dried over sodium sulfate and concentrated to dryness to obtain 2-iodo-3-methylbenzyl alcohol as off-white solid (1.2 g); 1H NMR (CDCI3, 300 MHz) delta 1.92 (broad, 1 H), 2.47 (s, 3H)1 4.71 (s, 2H), 7.15- 7.32 (m, 3H).

The synthetic route of 108078-14-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2006/50843; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6293-83-0, 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. 6293-83-0 name is 2-Iodo-4-nitroaniline, 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.

N-Benzyl-5-bromo-2-iodobenzamide (805 mg, 1.93 mmol), 2-iodo-4-nitroaniline (425 mg, 1.61 mmol), copper(I) iodide (123 mg, 0.65 mmol), and potassium carbonate (1.11 g, 8.0 mmol) were taken up in anhydrous DMSO (11 muL). The resulting reaction mixture was first stirred at 80C for 2 hr, followed by heating to 135 C for another 16 hr. After cooling to room temperature, the mixture was diluted with an excess of Et2O and washed with water. The organic layer was dried over Na2S04, fdtered and concentrated. The residue was purified by flash column chromatography (EtOAc : Hex = 0 : 100 to 100 : 0) to give 10-benzyl-2-bromo-8- nitro-5, 10-dihydro- 11H-dibenzo[b,e][1,4]diazepin-11-one (179 mg, 26 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-4-nitroaniline, and friends who are interested can also refer to it.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164932; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

88-67-5, 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. 88-67-5, name is 2-Iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add compound 5 (8.44 g, 34.03 mmol) to a 250 ml round bottom flaskAnd 60ml concentrated sulfuric acid, stir to 60 C and add N-bromosuccinimide(4.82 g, 38.06 mmol), reacted for 2 h, and after cooling to room temperature, the solution was dropped into ice water.Extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure.Column chromatography gave 9.54 g of white solidCompound 6, yield 86%.

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

Reference:
Patent; Dalian University of Technology; Wang Shisheng; Li Guangzhe; Liu Liqiang; Zhao Weijie; Guo Xiuhan; Li Yueqing; Wang Xu; Dong Huijuan; (21 pag.)CN110041200; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2401-21-0, These common heterocyclic compound, 2401-21-0, name is 1,2-Dichloro-3-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.

Method C 2,3-Dichloroiodobenzene (350 g, 1.282 mol) dissolved in dry ether (1250 ml) was added slowly, with stirring, to magnesium turnings (30.77 g, 1.282 mol) in dry diethyl ether (300 ml), in order to form 2,3-dichlorophenylmagnesium iodide under nitrogen.

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 2401-21-0.

Reference:
Patent; Glaxo Wellcome Inc.; US5912345; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, 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. 31599-60-7

To a solution of 1-iodo-2,3- dimethylbenzene (8) [prepared according to Chen, Y et al. Org. Lett. 2007, 9, 1899] (1 .93 g, 8.32 mmol) in carbon tetrachloride (40 mL) was added NBS (3.67 g, 20.62 mmol), AIBN (0.070 g, 0.43 mmol) and the resulting mixture was gently refluxed by irradiation with a halogen lamp (500 W) for 4 h. The precipitate was filtered and washed with a small amount of carbon tetrachloride. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc ( 1 00 ml), successively washed with 10% NaOH solution (20 mL), water (2 x 20 ml), 10% Na2S203 solution (20 mL), water (20 mL), brine (20 raL), and dried (Na2SC>4). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether) to give 1 .89 g (58.3%) of compound 9. NMR (CDC13) delta: 7.84 (dd, J=8.1 , 1 .1 Hz, 1 H), 7.33 (dd, J=7.6, 1 .1 Hz, l H), 6.97 (t, J=7.8 Hz, 1 H), 4.85 (s, 2H), 4.66 (s, 2H). The product contained ca. 15-20% of an inseparable impurity (supposedly l -bromo-2,3-bis(bromomethyl)benzene).A mixture of 1,2-bis(bromomethyl)-3-iodobenzene (9) (2.50 g, 6.41 mmol), diethyl 2-acetamidomalonate (1 .39 g, 6.41 mmol), and K2C03 (2.22 g, 1 6.06 mmol) in acetonitrile (40 mL) was refluxed for 70 h. The mixture was allowed to cool to ambient temperature, the precipitate was filtered and washed with a small amount of acetonitrile. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc (100 mL), washed successively with saturated NaHC03 solution (30 mL), water (2 x 30 mL), brine (30 mL), and dried (Na2S04). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 2 g of oil. The oil was dissolved in diethyl ether and kept in a refrigerator overnight. The precipitate was filtered and dried to give 0.4 g (14%) of a regioisomer diethyl 2-acetyl-5-iodo-l ,4-dihydroisoquinoline-3,3(2H)-dicarboxylate. NMR (CDC13) delta: 7.76 (d, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1 H), 6.94 (t, J = 7.7 Hz, 1H), 4.65 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.56 (s, 2H), 2.28 (s, 3H), 1 .22 (t, J=7.1 Hz, 3H), 1.22 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z: 446 [M+H]+. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 0.95 g (33.2%) of compound (10).A solution of diethyl 2-acetyl-8-iodo-l,4-dihydroisoquinoline-3,3(2H)-dicarboxylate (10) (0.585 mmol) in 6 N HQ (10 mL) was refluxed for 5 h. The mixture was cooled and cone. NH4OH water solution was added until pH of the medium was ~7. The precipitate was filtered, washed with a small amount of water, and dried to give 0.305 g (76.7%) of compound (11). Because of a low solubility of the product in common deuterated organic solvents and deuterium oxide, the NMR spectrum was not informative. LCMS (ESI) m/z: 304 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid). LCMS (ESI) m/z: 256 [M+H]+.To a suspension of 8-iodo-l ,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (11) (0.645 g, 2.13 mmol) in methanol ( 1 8 mL) slowly SOCI2 ( 1.07 ml, 14.92 mmol) was added within 10 min. The reaction mixture was stirred at room temperature for 16 h, evaporated, and the residue was dissolved in a mixture of IN NaHC03 solution (30 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 ^ 15 mL). The organic extracts were combined, washed successively with water (20 mL), brine (20 mL), and dried (Na2S04). The solvents were evaporated to give compound 12 (0.570 g, 84%) which was used in the next step without further purification. NMR (CDCI3) delta: 7.67 (d, J=7.8 Hz, IH), 7.10 (d, J=7.5 Hz, I H), 6.87 (t, J=7.7 Hz, IH), 4.07 (d, 16.6 Hz, IH), 3.87 (d, J=16.6 Hz, I H), 3.78 (s, 3H), 3.71 (dd, J=9.4, 5.0 Hz, I H), 3.04 (dd, J=16.5, 5.0 Hz, IH), 2.97 (dd, J=l 6.5, 9.4 Hz, IH). LCMS (ESI) m/z: 318 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative methyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate). LCMS (ESI) m/z: 270 [M+H]+.A mixture of methyl 8-iodo-1, 2,3,4- tetrahydroisoquinoline-3-carboxylate (12) (0.570 g, 1 .8 mmol) and 2,3-dichloro-5,6-dicyano- 1 ,4-benzoquinone (DDQ) (0.449 g, 2.0 mmol) in toluene (20 mL) was refluxed for 6 h. To the reaction mixture was added another portion of DDQ (0.100 g, 0.45 mmol) and the refluxing was continued for 16 h. The mixture was allowed to cool to room temperature; the precipitate was filtered and washed with a small amount of toluene. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 100:0 to 100: …

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 31599-60-7.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

696-41-3, Adding some certain compound to certain chemical reactions, such as: 696-41-3, name is 3-Iodobenzaldehyde, 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 696-41-3.

General procedure: A mixture of an aldehyde (1) (1.0 equiv), 2-aminobenzophenone (2) (1.0equiv), NH4OAc (3) (2.0 equiv), and DMAP (0.2 equiv.) in absolute EtOH (5 ml)was stirred at 40 C for the stipulated period of time (see Tables 2 and 3). Aftercompletion of the reaction, as monitored by TLC, the mixture was poured intoice-cold H2O and the solid product was filtered, washed with H2O (3-5 mL) anddried. The crude product was recrystallized from EtOAc to give puredihydroquinazolines. For compounds 4c, 4g, 4m, and 4p, after cooling, H2Owas added and the product was extracted with EtOAc (3 15 mL). Thecombined organic extract was washed with H2O, dried (anhyd Na2SO4) and thesolvent removed followed by flash column chromatography over silica gel (60-120 mesh) to furnish the desired 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 696-41-3.

Reference:
Article; Derabli, Chamseddine; Boulcina, Raouf; Kirsch, Gilbert; Carboni, Bertrand; Debache, Abdelmadjid; Tetrahedron Letters; vol. 55; 1; (2014); p. 200 – 204;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

34683-73-3, name is 1-Chloro-6-iodohexane, 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. 34683-73-3

5-(7-Chloroheptyl)-3-methyl-isoxazole (VIII) 21.0 g (0.216 mol) of 3,5-dimethylisoxazole (VII) (prepared in accordance with the method of C. Kashima et al., Bull. Chem. Soc. Jap. 46, 310, 1973) are dissolved in 200 ml of absolute tetrahydrofuran, the solution is cooled to -80 C. and 160 ml of n-butyllithium (1.35M solution in n-hexane, 0.216 mol) are added dropwise at this temperature in the course of 40 minutes. The mixture is stirred at a temperature below -75 C. for a further 15 minutes. The reaction mixture is then added dropwise to a solution of 53.5 g (0.217 mol) of 1-iodo-6-chlorohexane (prepared in accordance with the method of W. F. Huber, J. Am. Chem. Soc. 73, 2730, 1951) in 150 ml of absolute tetrahydrofuran so that the temperature does not rise above -60 C. When the addition has ended, the mixture is stirred at -60 C. for a further 15 minutes and allowed to warm to room temperature. The reaction mixture is partitioned between methylene chloride and 0.2N HCl, the aqueous phase is extracted three more times with methylene chloride and the combined organic phases are dried over sodium sulfate and evaporated. The crude product (about 45 g) is distilled in portions in a bulb tube (air bath temperature 80 C./0.2 mbar). Yield: 26.9 g of a yellowish oil.

Statistics shows that 34683-73-3 is playing an increasingly important role. we look forward to future research findings about 1-Chloro-6-iodohexane.

Reference:
Patent; Chemie Linz Akteingesellschaft; US4812472; (1989); A;,
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. 4102-53-8, name is 4-Iodo-2,6-dimethylaniline, A new synthetic method of this compound is introduced below., 4102-53-8

To a suspension of sodium bicarbonate (126 g, 1500 mmol) and 2,6-dimethylaniline (61.5 mL, 500 mmol) in methanol (700 mL) was added iodine monochloride (1.0 M in dichloromethane, 550 mL, 550 mmol) at room temperature over 1 h. After addition was complete, stirring was continued for 3 h. The reaction was filtered to remove excess sodium bicarbonate and the solvent removed in vacuo. The residue was redissolved in diethyl ether (1.5 L) and treated with hydrochloric acid (2M in ether, 375 mL, 750 mmol). The resulting suspension was stored in the freezer (-15 C.) overnight. The solid was filtered and washed with diethyl ether until it became colorless to give 126.5 g (89%) as a grey-green powder. 1H-NMR (DMSO-d6) delta 2.33 (s, 6H), 7.48 (s, 2H), 9.05 (bs, 3H); 13C-NMR (DMSO-d6) delta 17.4, 91.5, 133.1, 131.2, 136.9.

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; Chaturvedula, Prasad V.; Han, Xiaojan; Jiang, Xiang-Jun J.; US2006/122250; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 35944-64-0, name is 3-Iodo-4-methylaniline, 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 35944-64-0. 35944-64-0

2/6-Difluoro-N-(2′-methyl-5I-(pyridin-2-ylmethoxy)biphenyl-4-yl)benza?iotaide[00150] To a solution of 3-iodo-4-methylaniline (1 g, 4.29 mmol) in H2O (25 mL) was added H2SO4 (0.5 M, 25 mL). The solution was heated to 8O0C until all solid dissolved. Then the reaction was cooled to 00C, and NaNCh (0.44 g, 6.39 mmol) was added in small portions. After 2 hr at this temperature, urea (0.13 g, 2.1 mmol) was added at 00C. The solution was allowed to warm up to room temperature, and H2SO4 (0.5 M, 25 mL) was added. The reaction was refluxed for 30 min and cooled down to room temperature. The solution was extracted with EtOAc and EbO, and the combined organic phases were dried over Na2SO4, concentrated, and chromatographied to give the pure product 1 (0.8 g, 80%). Following the general Suzuki coupling procedure, 2 was prepared.[00151] The solution of 2 (0.4 g, 1.18 mmol), 2-picolyl chloride hydrochloride (0.215 g, 1.31 mmol), and K2CO3 (0.325 g, 2.35 mmol) in DMF (5 mL) was heated at 500C for 48 hr. The reaction solution was diluted with H2O (15 mL) and extracted with EtOAc (25 mL). Column chromatography (Hexanes/EtOAc=l/l) afforded Compound 4 in 56% yield.[00152] 1H NMR (400 MHz, CDCl3) delta 8.59 (d, / = 4.8 Hz, 1 H), 7.74-7.66 (m, 4 H), 7.55-7.52 (m, 1 H), 7.48-7.40 (m, 1 H), 7.34-7.32 (m, 2 H), 7.24-7.16 (m, 2 H), 7.02 (t, / = 8.0 Hz, 2 H), 6.90-6.87 (m, 2 H), 5.21 (s, 2 H), 2.21 (s, 3 H); ESMS cacld (C26H20F2N2O2): 430.1; found: 431.1 (M+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 3-Iodo-4-methylaniline.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; JIANG, Jun; ZHANG, Junyi; CHEN, Shoujun; SUN, Lijun; WO2010/39238; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com