Tag: M.W=300-400

Synthetic Route of 755027-18-0, 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. 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of PdCl2(dppf)-CH2Cl2 adduct (0.065 g, 0.080 mmol), l-bromo-4-iodo- 2-methoxybenzene (CombiBlocks, 0.250 g, 0.799 mmol), 3-fluorophenylboronic acid (0.123 g, 0.879 mmol) and potassium phosphate (0.848 g, 3.99 mmol) in dioxane (2.130 ml)/water (1.065 ml) was heated to 90 C overnight. The reaction was diluted with DCM and separated from the aqueous via phase separator (Radleys Discovery Technologies). After concentration in vacuo, the material was purified via MPLC (12-g Redi Sep Gold), eluting with 0-100% ethyl acetate in heptanes to yield, after concentration, 4-bromo-3 ‘-fluoro-3 -methoxy- 1,1’- biphenyl as an orange oil, which was used without further purification.

The synthetic route of 1-Bromo-4-iodo-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; BOEZIO, Christiane; BOEZIO, Alessandro; BREGMAN, Howard; CHAKKA, Nagasree; COATS, James R.; COPELAND, Katrina W.; DIMAURO, Erin F.; DINEEN, Thomas; GAO, Hua; LA, Daniel; MARX, Isaac E.; NGUYEN, Hanh Nho; PETERSON, Emily Anne; WEISS, Matthew; WO2013/122897; (2013); A1;,
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Electric Literature of 51560-21-5,Some common heterocyclic compound, 51560-21-5, name is 1,4-Diiodo-2,5-dimethoxybenzene, molecular formula is C8H8I2O2, 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: according to the Mizoroki-Heck reaction (Scheme 1). First; by thecoupling between 4-substituted styrenes and dibromo or diiodobenzenes(Method A, Scheme 1), and second; the reaction between4-substituted bromo or iodobenzenes with 1,4-divinylbenzene(Method B, Scheme 1).The general procedure is as follows: 2.05 equivalents of thecorresponding styrene and 1 equivalent of 1,4-dibromo or 1,4-diiodobenzene (Method A, to OPVs 1a-d and 2a-f) or 2.05 equivalentsof the appropriate aryl halide and 1 equivalent of 1,4-divinylbenzene (Method B, to OPVs 1e-h), were placed in a 10 mLheadspace crimp vial equipped with a magnetic stir bar. Then, forboth methods, it was added 0.01 equivalents (1 mol%) of Pd(dba)2,0.1 equivalents (10 mol%) of P(OPh)3 and 5 equivalents of TEA. Thevial was sealed with a PTFE/silicone septum with aluminum capand purged-saturated with N2, then 2 mL of solvent was injected(dry DMF for OPVs-series 1 and 1,4-dioxane for OPVs-series 2,Scheme 1) and the system was purged once again with N2. Thereaction mixture was vigorously stirred at 110 C during 48 h forOPVs-series 1 and 24 h for OPVs-series 2. After finished, highlyfluorescent solid products were obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Diiodo-2,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Estrada, Sandra E.; Ochoa-Puentes, Cristian; Sierra, Cesar A.; Journal of Molecular Structure; vol. 1133; (2017); p. 448 – 457;,
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148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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. Recommanded Product: 148870-57-9

Based on EP 0 534 859 [0053] A solution of the (d) camphorsulphonate salt obtained in Example 4 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. [0054] A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. [0055] The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. [0056] The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. [0057] Yield=64%

The synthetic route of 148870-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; CARRANZA, Maria Del Pilar; GARCIA ARANDA, Maria Isabel; GONZALEZ, Jose Lorenzo; SANCHEZ, Frederic; US2014/163220; (2014); A1;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1022128-96-6, name is 2-Bromo-6-iodobenzoic acid, 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 1022128-96-6, COA of Formula: C7H4BrIO2

9.1 (7.32 g, 22 mmol) was dissolved in 40 mL of tetrahydrofuran, 4 mL of thionyl chloride and a catalytic amount of N,N-dimethylformamide After reacting for 3 hours, the reaction solution was spun off, and the residue was added with 40 mL of tetrahydrofuran, and ammonia was added dropwise with stirring in an ice bath. 33 mL of water was allowed to stand at room temperature for 3 hours. Extract with ethyl acetate and wash with saturated sodium bicarbonate. The organic layer is dry and concentrated. With a small amount of dichloromethane and purified by recrystallization from n-hexane to give a large number of white solid 9.2 6.09g, the yield was 85%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-6-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; East China University of Science and Technology; Wang Wei; Chen Xiaobei; Shen Zuyuan; Qian Pengfei; Geng Huihui; (24 pag.)CN109942505; (2019); A;,
Iodide – Wikipedia,
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Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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. COA of Formula: C7H4BrIO2

5-Bromo-2-iodobenzoic acid (7c) (750 mg, 2.3 mmol) was dissolved in dry THF (25 mL) and the reaction mixture was cooled to 0 C. NEt3 (0.48 mL, 3.4 mmol) and ethyl chloroformate (0.33 mL, 3.4 mmol) were added and the reaction mixture was stirred for 1 hour. Next a solution of NaBH (130 mg, 3.4 mmol) in H20 (2 mL) was added and the mixture was stirred for 1.5 hour. The reaction was quenched with H20 (15 mL), whereupon CH2C12 (20 mL) was added and the layers were separated. Hereupon, the H20-layer was extracted with CH2C12 (20 mL). Subsequently, the combined organic layers were washed with H20 (25 mL) and brine (25 mL), dried over MgS04 and concentrated in vacuo. The crude product was purified by gradient column chromatography (-heptane/EtOAc, 19: 1 to 9: 1) to obtain compound 7c as a white solid (410 mg, 54% over 2 steps). RF = 0.40 (EtOAc/-heptane, 1 :4). 1H- NMR (400 MHz, CDC13) delta: 7.65 (d, J = 8.3 Hz, 1H), 7.63 (d, J = 2.4 Hz, 1H), 7.14 (dd, J = 8.3, 2.5 Hz, 1H), 4.64 (d, J = 6.1 Hz, 2H), 1.96 (t, J = 6.2 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21740-00-1, its application will become more common.

Reference:
Patent; STICHTING KATHOLIEKE UNIVERSITEIT; SYNAFFIX B.V.; DEBETS, Marjoke Froukje; RUTJES, Floris Petrus Johannes Theodorus; VAN HEST, Jan Cornelis Maria; VAN DELFT, Floris Louis; VAN BERKEL, Sander Sebastiaan; WO2014/189370; (2014); A1;,
Iodide – Wikipedia,
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Related Products of 628-77-3, 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 628-77-3 as follows.

Example 1.12: Preparation of 2′,3′,4′,4a’,5′,6′-hexahydro-l’/ -spiro[cyclohexane-l,7′- naphtho[l,8-cd]azepine] (Compound 117) Step A: Preparation of 3′,4′-dihyd ‘/ -spiro[cyclohexane-l,l’-naphthalen]-2′-one To a suspension of 60% sodium hydride dispersion (1.2 g, 30.00 mmol) in 70 mL THF, a solution of 3,4-dihydronaphthalen-2(lH)-one (2.0 g, 13.68 mmol) in 30 mL THF was added (over ca. 5 min). After stirring at room temperature for 10 min, 1,5-diiodopentane (2.04 mL, 13.71 mmol) was added. After stirring at room temperature overnight, the mixture was partly concentrated and residue was extracted with water and AcOEt. Organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by biotage column chromatography (S1O2, hexane/ AcOEt gradient) to give 3′,4′-dihydro-2’H-spiro[cyclohexane-l,r-naphthalen]-2′-one (2.24 g, 76%) as a colorless oil. NMR (400 MHz, CDCI3) delta 1.27-1.39 (m, 1H), 1.62-1.79 (m, 7H), 2.10-2.17 (m, 2H), 2.70 (t, / = 7.1 Hz, 2H), 3.19 (t, / = 7.2 Hz, 2H), 7.12 (m, 2H), 7.22-7.27 (m, 1H), 7.38-7.40 (m, 1H).

According to the analysis of related databases, 628-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; LEHMANN, Juerg; FEICHTINGER, Konrad; REN, Albert S.; SEMPLE, Graeme; (205 pag.)WO2017/23679; (2017); 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. 811842-30-5, name is 2-Bromo-1-fluoro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 811842-30-5

Into a 1 L four-necked round bottom flask equipped with a stirrer, an Erlin condenser, a nitrogen inlet tube, and a thermometer, 23.2 g (101.8 mmol) of 4-dibenzothiopheneboronic acid of Synthesis Example 9,33.6 g (111.9 mmol) of 3-bromo-4-iodo-1-fluorobenzene of Synthesis Example 23, 340 mL of toluene, 170 mL of ethanol,28.0 g (202.6 mmol) of potassium carbonate and 90 mL of water were placed, and the mixture was stirred at room temperature for 30 minutes under a nitrogen stream.Subsequently, 0.11 g (0.50 mmol) of palladium acetate and 0.30 g (0.98 mmol) of tri (o-tolyl) phosphine were added and heated, followed by stirring at a reflux temperature for 2 hours. The resulting reaction solution was cooled to room temperature, the aqueous layer was separated, and extracted with 150 mL of ethyl acetate. Then, the organic layers were combined, washed with 150 mL of saturated brine, dried with magnesium sulfate, magnesium sulfate was removed by suction filtration, and the solvent was distilled off under reduced pressure. Subsequently, the resulting oil was purified by recrystallization using a mixed solvent of n-heptane and toluene to obtain 18.4 g (yield 53.0%) of the objective compound.

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 811842-30-5.

Reference:
Patent; YAMAGATA UNIVERSITY; CHEMIPRO KASEI KAISHA LIMITED; KIDO, JUNJI; SASABE, HISAHIRO; TAKAHASHI, JUN; NAGAI, NAGAI; (723 pag.)JP2018/90561; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 16355-92-3, The chemical industry reduces the impact on the environment during synthesis 16355-92-3, name is 1,10-Diiododecane, I believe this compound will play a more active role in future production and life.

2-Picoline (0.30 mL, 3.1 mmol) and 1,10-diiododecane (13.0 g, 33 mmol) were dissolved in acetone (20 mL) with a 50 mL flask equipped with a condenser. The solution was heated to reflux at 60C for 4 days. The solution was dropped into hexane (300 mL), and then a yellow precipitate was obtained. The precipitate was recovered and dried to obtain the product 4 as yellow powder (yield 1.3 g, 87%). 1H NMR (500MHz, DMSO-d6): delta 8.96 (d, J=5.1Hz, 1H), 8.44 (t, J=7.8Hz, 1H), 8.02 (d, J=7.9Hz, 1H), 7.94 (t, J=6.8Hz,1H), 4.51 (t, J=7.8Hz, 2H), 3.25 (t, J=6.8Hz, 2H), 2.82 (s, 3H), 1.85-1.79 (m, 2H), 1.75-1.69 (m, 2H), 1.36-1.22 (m, 12H).

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, 1,10-Diiododecane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hashidzume, Akihito; Kuse, Akihiro; Oshikiri, Tomoya; Adachi, Seiji; Yamaguchi, Hiroyasu; Harada, Akira; Tetrahedron; vol. 73; 33; (2017); p. 4988 – 4993;,
Iodide – Wikipedia,
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Electric Literature of 98-61-3, 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. 98-61-3, name is 4-Iodobenzenesulfonyl chloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5.1.11 N-[(5-Isobutyl-1-phenyl-1H-pyrazol-3-yl)methyl]-4-iodobenzenesulfonamide (9d) Triethylamine (32.6 muL, 0.234 mmol) was added at 0 C to a solution of (5-isobutyl-3-aminomethyl-1-phenyl)pyrazole (48.7 mg, 0.212 mmol) in dichloromethane (1.0 mL). The solution was stirred for 5 min, and mixed with a solution of 4-iodobenzenesulfonyl chloride (68.2 mg, 0.223 mmol) in dichloromethane. Subsequently, the solution was warmed to room temperature, and stirred for 1 h. Then, water and a saturated sodium hydrogen carbonate solution were added to the solution before extraction with dichloromethane. The organic layer thus formed was dried over magnesium sulfate, concentrated in vacuo, and purified by column chromatography (hexane:EtOAc = 3:1 ? 2:1) to afford the title compound (86.3 mg, 82.0%). 1H NMR (400 MHz, CDCl3) delta 7.76 (d, J = 8.16 Hz, 2H), 7.53 (d, J = 8.24 Hz, 2H), 7.46-7.38 (m, 3H), 7.23 (d, J = 7.60 Hz, 2H), 5.95 (s, 1H), 5.72 (br, 1H), 4.18 (d, J = 5.80 Hz, 2H), 2.40 (d, J = 7.16 Hz, 2H), 1.75-1.68 (m, 1H), 0.81 (d, J = 6.60 Hz, 6H); 13C NMR (100 MHz, CDCl3) delta 147.6, 144.4, 139.9, 139.5, 138.1, 129.2, 128.7, 128.2, 125.7, 104.8, 99.7, 41.0, 35.0, 28.3, 22.4.

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, 4-Iodobenzenesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kim, Jung Hyun; Keum, Gyochang; Chung, Hesson; Nam, Ghilsoo; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 665 – 672;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 162358-07-8, A common heterocyclic compound, 162358-07-8, name is 1-(2-Iodoethyl)-4-octylbenzene, molecular formula is C16H25I, 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 16 Production of diethyl acetamido-2-(4-octylphenyl)ethylmalonate (8) [Step (H)] To a solution of diethyl acetamidomalonate (277 g) and sodium ethylate (86.6 g) in anhydrous ethanol (850 ml) is added a solution of 2-(4-octylphenyl)ethyl iodide (7) (146 g) in anhydrous tetrahydrofuran (533 ml), and the mixture is refluxed under heating for 6 hr. The reaction mixture is concentrated and partitioned between water and hexane, and the hexane layer is washed three times with water. The obtained hexane layer is dried over anhydrous magnesium sulfate and concentrated. The residue is recrystallized from hexane to give the title compound (8) as colorless crystals. The resulting Compound (8) has the same physico-chemical characteristics as indicated in Example 7.

The synthetic route of 162358-07-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abel, Stephan; Fujita, Tetsuro; Hirose, Ryoji; Jordine, Guido; Mishina, Tadashi; US2002/72635; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com