Category: iodides-buliding-blocks

Some common heterocyclic compound, 755027-18-0, name is 1-Bromo-4-iodo-2-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. Recommanded Product: 1-Bromo-4-iodo-2-methoxybenzene

Step 2: ethyl 2-(4-bromo-3-methoxyphenyl)cyclohex-1-ene-1-carboxylate To a solution of the product from Step 1, ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-ene-1-carboxylate (6.65 g, 22.0 mmol) in dioxane (125 mL) was added potassium carbonate (4.56 g, 33.0 mmol), PPh3 (0.346 g, 1.32 mmol), bis(pinacolato)diboron (6.15 g, 24.20 mmol), and PdCl2(PPh3)2 (0.463 g, 0.66 mmol). The mixture was then heated to 80 C. overnight. This solution was then cooled to r.t. and added to a mixture of 1-bromo-4-iodo-2-methoxybenzene (6.86 g, 21.92 mmol), PdCl2(dppf) (0.481 g, 0.657 mmol), potassium carbonate (9.09 g, 65.7 mmol). This mixture was then heated to 80 C. overnight. The mixture was then cooled to r.t., diluted with EtOAc (300 mL) and washed with brine and aqueous KHSO4. The organic layer was then dried over Na2SO4 and the solvent was removed in vacuo. The crude material was then purified on silica (100% DCM) to give impure product which was repurified on silica (gradient elution, 5-20% EtOAc/hexanes) to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 755027-18-0, its application will become more common.

Reference:
Patent; Harper, Steven; Summa, Vincenzo; Liverton, Nigel J.; McCauley, John A.; Butcher, John W.; Di Filippo, Marcello; Di Francesco, Maria Emilia; Ferrara, Marco; Romano, Joseph J.; Rudd, Michael T.; US2010/183551; (2010); A1;,
Iodide – Wikipedia,
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Electric Literature of 17024-12-3, The chemical industry reduces the impact on the environment during synthesis 17024-12-3, name is 9-Iodophenanthrene, I believe this compound will play a more active role in future production and life.

10261] Into an 80-mE flask were put 3.27 g (17 mmol) of3-chlorobenzamidine hydrochloride, 5.2 g (17 mmol) of 9-io- dophenanthren, 0.31 g (1.6 mmol) of copper iodide, 16 g (49 mmol) of cesium carbonate, 0.29 g (3.3 mmol) of N,N-dimethylethylenediamine, and 80 mE of dimethylformamide (DMF), and the air in the flask was replaced with nitrogen. The mixture in the flask was stirred at 1000 C. for 21 hours. Then, 0.31 g (1.6 mmol) of copper iodide and 0.29 g (3.3 mmol) of N,N-dimethylethylenediamine were added, and the mixture was stirred at 110 C. for 8.5 hours. The resulting solution was subjected to suction filtration, and the obtained solid was washed with toluene. The obtained filtrate was washed with water, and the organic layer was washed with saturated saline. Magnesium sulfate was added to the organic layer for drying, and the resulting mixture was subjected to gravity filtration to give a filtrate. The filtrate was condensed to obtain an objective substance (a brown oily substance, at a yield of 50%). The synthesis scheme of Step 1 is shown in (a-i).

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, 9-Iodophenanthrene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; HARA, Tomoka; INOUE, Hideko; TAKAHASHI, Tatsuyoshi; HAMADA, Takao; SEO, Satoshi; (60 pag.)US2016/190479; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 69113-59-3, These common heterocyclic compound, 69113-59-3, name is 3-Iodobenzonitrile, 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.

General procedure: Step 1: 3-{[1-(6,7-dimethoxyquinazolin-4-yl)piperidin-4-yl]methyl}-3,4-dihydroquinazolin-2(1H)-one (50 mg, 0.12 mmol) obtained by the method described in Chemical & Pharmaceutical Bulletin 1990, 38(6), 1591, copper(I) iodide (22 mg, 0.12 mmol), trans-1,2-cyclohexanediamine (13 mg, 0.12 mmol), 3-iodobenzonitrile (53 mg, 0.23 mmol) and tripotassium phosphate (49 mg, 0.23 mmol) were stirred in 1,4-dioxane (1.0 mL) at 100 C. for 5 hours. To the reaction mixture, a saturated aqueous sodium bicarbonate solution was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was treated with diatomaceous earth and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (a chloroform/methanol mixed solvent), whereby the title Compound 6 (51 mg, yield: 82%) was obtained. ESI-MS m/z: 535 (M+H)+, 1H-NMR (300 MHz, CDCl3, delta): 8.66 (s, 1H), 7.73-7.59 (m, 4H), 7.24 (s, 1H), 7.16-7.00 (m, 4H), 6.17 (d, J=8.4 Hz, 1H), 4.62 (s, 2H), 4.24-4.14 (br m, 2H), 4.02 (s, 3H), 3.98 (s, 3H), 3.47 (d, J=7.3 Hz, 2H), 3.10-3.06 (br m, 2H), 2.18-2.10 (m, 1H), 1.93-1.90 (m, 2H), 1.62-1.54 (m, 2H)

The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYOWA HAKKO KIRIN CO., LTD.; ISHIDA, Hiroshi; MOTOSAWA, Keiichi; MIURA, Yusuke; NAKAI, Ryuichiro; OKADA, Ryoko; TAKAHASHI, Yuichi; (45 pag.)US2016/168125; (2016); A1;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, 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 20555-91-3, Safety of 1,2-Dichloro-4-iodobenzene

INTERMEDIATE 5: 1-[3-(3,4-dichlorophenyl)prop-2-yn-1-yl]-1H-indole-2,3-dione To a mixture of 1-prop-2-yn-1-yl-1H-indole-2,3-dione (190 mg, 1.03 mmol), 1,2-dichloro-4-iodobenzene (420 mg, 1.54 mmol), copper(I) iodide (1 1.0 mg, 0.06 mmol) and triphenylphosphine (40.0 mg, 0.15 mmol) in degassed DMF (24 mL) was added triethyl-amine (307 muL, 2.15 mmol). The reaction was stirred for 5 minutes and Pd(OAc)2 (13.0 mg, 0.06 mmol) was then added. The reaction was stirred at room temperature for 2 days, concentrated in vacuo, dissolved in EtOAc and washed with saturated NaHCO3(aq) (1¡Á). The layers were separated and the aqueous layer was extracted with additional EtOAc (2¡Á). The combined organic phases was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with a solvent gradient of 35% EtOAc/Hexanes to 75% EtOAc/Hexanes, to give the title compound as an orange solid with 90% purity (375 mg, quantitative yield). 1H NMR (400 MHz, DMSO-D6) delta 4.82 (s, 2H), 7.18 (dt, J=7.52, 0.78 Hz, 1H), 7.32 (d, J=8.01 Hz, 1H), 7.41 (dd, J=8.40, 1.95 Hz, 1H), 7.60 (dd, J=7.42, 0.78 Hz, 1H), 7.63 (d, J=8.40 Hz, 1H), 7.70-7.75 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Dichloro-4-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; US2007/185179; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 98-61-3,Some common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, molecular formula is C6H4ClIO2S, 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.

18-Crown-6 (0.5 g) and potassium fluoride (11.6 g, 200 mmol) were added to a solution of iodobenzenesulphonyl chloride (30.3 g, 100 mmol) in acetonitrile (100 ml) and the suspension was stirred for 18 hours at ambient temperature. The insolubles were removed by filtration and the solvent removed from the filtrate by evaporation. The residue was dissolved in EtOAc (300 ml), washed with water (2*150 ml), brine (100 ml), dried and the solvent evaporated to give the title compound (27.54 g, 96%) as a white solid. NMR 7.70 (d, 21H), 8.01 (d, 2H); m/z 286.

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

Reference:
Patent; Breault, Gloria Anne; Newcombe, Nicholas John; Thomas, Andrew Peter; US2004/14776; (2004); A1;,
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. 2265-91-0, name is 1,3-Difluoro-5-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H3F2I

General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33 mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11 mmol) in DMF (20 mL) were added substituted iodobenzene (2.21 mmol) and 4-acetyloxystyrene (2.44 mmol). The reaction mixture was recharged with Argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford the intermediate substituted (E)-4-styrylphenyl acetate. To a solution of triethylamine (2.0 mL) in MeOH (5 mL) was added substituted (E)-4-styrylphenyl acetate (1.36 mmol). The reaction mixture was stirred at reflux temperaturefor 3 h. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol, 10:0.3) to afford pure product.

The synthetic route of 2265-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jian-Hua; Yang, Liang; Wu, Si; Liu, Si-Si; Cushman, Mark; Tian, Jing; Li, Nuo-Min; Yang, Qing-Hu; Zhang, He-Ao; Qiu, Yun-Jie; Xiang, Lin; Ma, Cong-Xuan; Li, Xue-Meng; Qing, Hong; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 382 – 392;,
Iodide – Wikipedia,
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Reference of 88-67-5, These common heterocyclic compound, 88-67-5, name is 2-Iodobenzoic acid, 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.

General procedure: To a stirred solution of different benzoic acids (6.42 mmol) in ethanol (3 mL) was added H2SO4 (0.1mL) and heated to reflux for 6-10 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was washed with saturated NaHCO3 followed by water and brine solution. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain the respective ethyl benzoate derivatives.

The synthetic route of 88-67-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Prasanna, V. Laxmi; Narender; Asian Journal of Chemistry; vol. 27; 10; (2015); p. 3605 – 3608;,
Iodide – Wikipedia,
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Electric Literature of 629-09-4, 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. 629-09-4, name is 1,6-Diiodohexane, This compound has unique chemical properties. The synthetic route is as follows.

Example 108: 2-Chloro-3-[l-(4-chlorophenylsulfonyl) cycloheptyl]pyridine At -78C, butyl lithium (a 1.57M hexane solution; 0.62 ml, 0.966 mmol) was added dropwise to a dimethoxyethane (5 ml) solution of the 2-chloro-3-(4-chlorophenylsulfonylmethyl)pyridine (146 mg, 0.483 mmol) obtained in Example 98.. At -78C, the resulting mixture was stirred for 20 minutes, followed by the addition of 1,6-diiodohexane (0.095 ml, 0.580 mmol).. The temperature of the reaction mixture was gradually raised to room temperature, at which stirring was performed for 4 hours. water was added to the reaction mixture, followed by extraction with ethyl acetate.. The organic layer was washed with brine and then dried over anhydrous sodium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the 15% ethyl acetate/hexane elude was concentrated under reduced pressure.. The residue thus obtained was purified by high performance liquid chromatography (using a mixed solvent of water/acetonitrile/formic acid) to yield the title compound (60 mg, 32%) as a white solid.. The resulting solid was washed with hexane-ether and then collected by filtration, whereby the title compound was obtained as a white powder.. Melting point: 168-169C. IR (ATR) nu: 2929, 2861, 1573, 1558, 1473, 1454, 1394, 1303, 1276, 1139, 1083, 1066, 1008, 840, 800, 748, 711, 646, 613, 574, 522, 470, 412 cm-1.1H-NMR (400MHz, CDCl3) delta: 1.30-1.50(4H,m), 1.50-1.66(2H,m), 1.85-1.98(2H,m), 2.33-2.48(2H,m), 2.94-3.10(2H,m), 7.28-7.37(3H,m), 7.40(2H,d,J=8.8Hz), 7.93(1H,dd,J=8.1,1.7Hz), 8.38(1H,dd,J=4.5,1.8Hz). MS (m/z): 384 (M++H). Elemental Analysis for C18H19Cl2NO2S Calculated: C 56.25%; H 4.98%; Cl 18.45%; N 3.64%; S 8.34%. Found: C 56.20%; H 4.85%; Cl 18.50%; N 3.73%; S 8.46%.

The chemical industry reduces the impact on the environment during synthesis 1,6-Diiodohexane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
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. 35944-64-0, name is 3-Iodo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 35944-64-0

4-(4-methylpiperazin-1-yl-methyl)-3-trifluoromethyl-benzoic acid (0.755 g, 2.5 mmol, 1.0 eq), HATU (O-(7-azabenzotriazol-1-oxo)-N, N, N?, N?-tetramethyluronium hexafluorophosphate) (1.14 g, 3 mmol, 1.2 eq), DIPEA (1.29 g, 10 mmol, 4.0 eq) was dissolved in methylene chloride. The mixture was stirred at room temperature for 0.5 h and to the solution 3-iodo-4-methylaniline (582.6 mg, 2.5 mmol, 1.0 eq) was added. Then the mixture was stirred at 45 C. overnight, evaporated to dryness after the completion of the reaction, extracted with saturated aqueous sodium bicarbonate and methylene chloride 3 times. The organic layer was combined and concentrated under reduced pressure. The residue obtained was isolated by column chromatography to give the title product as a light yellow solid (892 mg, 69.0% yield). 1H NMR (400 MHz, CDCl3) 8.10 (s, 1H), 8.08 (d, J=2 Hz, 1H), 8.08-8.05 (m, 1H), 8.0 (s, 1H), 7.95 (s, 1H), 7.55 (dd, J=4, 2 Hz, 1H), 7.20 (d, J=8 Hz, 1H), 3.75 (s, 2H) 2.60-2.41 (m, 8H), 2.40 (s, 3H), 2.30 (s, 3H). MS m/z (ESI): 518.1 [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 35944-64-0.

Reference:
Patent; Si Chuan University; Yang, Shengyong; Wei, Yuquan; (168 pag.)US2017/305920; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 629-09-4, 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. 629-09-4, name is 1,6-Diiodohexane, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 25 1-[6-(2-methyl-1-imidazolyl)hexyl]-2-methylimidazole Stir overnight at room temperature, 10 ml. DMF, 1.18 gm. sodium hydroxide, 2.43 gm. 2-methyl imidazole and 1 gm. 1,6-diiodohexane in a reaction flask. Treat with methylene chloride and wash with water. Dry on sodium sulfate and remove the solvent to yield the title compound. Prepare the hydrochloride salt of the title compound by reacting with about 1 eq. of 0.1N hydrochloric acid.

The chemical industry reduces the impact on the environment during synthesis 1,6-Diiodohexane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Schering Corporation; US4851423; (1989); A;; ; Patent; Schering Corporation; US5272167; (1993); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com