Month: June 2021

Electric Literature of 6293-83-0,Some common heterocyclic compound, 6293-83-0, name is 2-Iodo-4-nitroaniline, molecular formula is C6H5IN2O2, 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: 2-iodoaniline (0.5 mmol) or 2-bromoaniline (0.5 mmol), complex 1 (0.05mmol), K2CO3 (1 mmol), (n-Bu)4NBr (0.1 mmol) and water (10 mL) were added to a sealed tube. The reaction mixture was stirred at 120oC for 30 h, then cooled to room temperature and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the solvent was then removed under reduced pressure. The product was finally obtained by column chromatography on silica gel.

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

Reference:
Short Survey; Yu, Lintao; Zhou, Xiangge; Wu, Di; Xiang, Haifeng; Journal of Organometallic Chemistry; vol. 705; (2012); p. 75 – 78;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 13194-69-9,Some common heterocyclic compound, 13194-69-9, name is 2-Iodo-5-methylaniline, molecular formula is C7H8IN, 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.

1-2 (0.0103 mol) was added drop wise to a mixture of 1-1 (0.0051 mol), Pd (PPh3) 2C12 (0.0005 mol) and GuI (0.0005 mol) in Et3N (15 ml) under N2 flow. The mixture was stirred at room temperature for 4 hours, poured into H20 and extracted with EtOAc. The organic layer was washed with H20, dried (over MgSO4), filtered and the solvent was evaporated_ The residue (2.1 g) was purified by column chromatography over silica gel (eluent: CHxClz/cyclohexane 70/30). The pure fractions were collected and the solvent was evaporated Yield: 1 g of intermediate 1-3 (79%).

The synthetic route of 13194-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58871; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 25245-35-6, These common heterocyclic compound, 25245-35-6, name is 2-Iodo-1,4-dimethoxybenzene, 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: 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 was subjected to chromatography (silica gel, hexane/ethyl acetate mixtures).

Statistics shows that 2-Iodo-1,4-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 25245-35-6.

Reference:
Article; Csuk, Rene; Albert, Sabrina; Siewert, Bianka; Schwarz, Stefan; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 669 – 678;,
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. 148836-41-3, name is 1-Bromo-4-chloro-2-iodobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-4-chloro-2-iodobenzene

The starting material 1-bromo-4-chloro-2-iodobenzene (1.58 g, 5.0 mmol), 4-chloro-1-ethynyl-2-methoxybenzene (916 g, 5.5 mmol), PdCl2(PPh3)2(70 mg, 0.1 mmol), CuI (19 mg, 0.05 mmol) and Et3N (20 mL) were stirred at room temperature for 24 hours under nitrogen. When the reaction is complete, extract the organic layer three times with diethyl ether. The extracted organic layer was dried over magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain Intermediate A-1 (1.60 g, 4.5 mmol, 90% yield). The resulting compound was identified via MS / FAB. C15H9BrCl2O cal. 356.04, found 353.92.

The synthetic route of 148836-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Display Co., Ltd.; Kim Hae-jin; Go Su-byeong; Jeon Mi-eun; Kim Yeong-guk; Hwang Seok-hwan; (70 pag.)KR2018/21340; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 13194-68-8 as follows. Safety of 4-Iodo-2-methylaniline

[00653] Example 4: 4-[(aminocarbonyl) amino]-1-(4-iodo-2- methylphenyl)-1 H-pyrazole-3-carboxamide; [00655] Step 1: Preparation of (2E)-2-cyano-2- [ (4-iodo-2- methylphenyl) hydrazono] acetamide; [00657] Preparation of Solution A: 2-Methyl-4-iodoaniline (23.3 g, 100 mmol) was treated with conc. HCI (25 mL) and diluted with water (100 mL). This mixture was stirred and cooled to-5 to 0C in an ice/acetone bath. To this was added a solution of sodium nitrite (6.90 g, 100 mmol) in water (20 mL) at-5 to 0C. The resultant mixture was stirred 20 min. To this was added a-5C solution of sodium acetate trihydrate (40.8 g, 300 mmol) in water (100 mL). [00658] Preparation of Solution B: Separately, cyanoacetamide (10.1 g, 120 mmol) was dissolved in water (180 mL) and ethanol (120 mL). The solution was cooled to-5C. To this was added a cooled (-5C) solution of sodium acetate trihydrate (13.6 g, 100 mmol) in water (30 mL). [00659] Solution A was added by pipette dropwise over about 30 min to Solution B at 5C to make a pasty mixture. After 3 h the mixture was filtered. The solids were then washed with ether (500 mL) and dried further to give a yellow brown solid. NMR indicated a mixture of stereomers.

According to the analysis of related databases, 13194-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/37797; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 618-91-7, A common heterocyclic compound, 618-91-7, name is Methyl 3-iodobenzoate, 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.

General procedure: A mixture ofmethyl 3-iodobenzoate (1 mmol), corresponding amine (3 mmol), K2CO3(4 mmol), CuI (0.2 mmol) and L-proline (0.4 mmol) in 15 mL of DMSO was heatedat 60 C for 8 h. The cooled mixture was pour into 150 ml water, and extractedwith ethyl acetate (3 × 15 mL), the organic fractions were combined, washedwith saturated brine (2 × 15 ml) prior to drying over anhydrous sodium sulfate.After filtration and concentrate using a rotary evaporator, the residue was purified by silica gel column chromatographyusing a mixture of petroleum ether/ethyl acetate (20 : 1, v/v) as eluent toafford the desired product.

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; Li, Zheng; Pan, Miaobo; Su, Xin; Dai, Yuxuan; Fu, Mian; Cai, Xingguang; Shi, Wei; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 1981 – 1987;,
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. 450412-29-0, name is 1-Bromo-3-fluoro-2-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 450412-29-0

To a stirred solution of 1-bromo-3-fluoro-2-iodobenzene (2.0 g, 6.7 mmol) in 1,4-dioxane (15 mL), were added dimethylphosphine oxide (0.62 g, 8.0 mmol), and K3PO4 (1.6 g, 7.3 mmol). The reaction mixture was purged with nitrogen for 5 min and charged with Xantphos (0.39 g, 0.67 mmol) and Pd2(dba)3 (0.30 g, 0.33 mmol). The reaction mixture was again purged with nitrogen for 3 min and heated at 100 C. for 9 h. The reaction mixture was filtered through Celite and concentrated under reduced pressure. The crude material was purified by column chromatography (0-100% EtOAc-Hexane, followed by 3% MeOH-CHCl3) to give Intermediate 16 (0.33 g, 1.3 mmol, 20% yield) as a yellow solid. MS(ESI) m/z: 250.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta=7.63 (d, J=8.0 Hz, 1H), 7.52 (td, J=8.0, 6.0 Hz, 1H), 7.43-7.28 (m, 1H), 1.87 (d, J=16.6 Hz, 3H), 1.86 (d, J=16.6 Hz, 3H).

The synthetic route of 450412-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Shirude, Pravin Sudhakar; Baligar, Vishweshwaraiah; Seshadri, Balaji; Chattopadhyay, Amit Kumar; Wurtz, Nicholas R.; Kick, Ellen K.; (91 pag.)US2019/270704; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 153898-63-6, The chemical industry reduces the impact on the environment during synthesis 153898-63-6, name is 2-Iodo-5-methoxyaniline, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 2-iodoanilines (1.0 mmol), THF (3 mL), and t-BuOK (3 mmol) was stirred in a 10-mL sealed Schlenk tube for 5 min, and then dimethylthiocarbamoyl chloride (1.2 mmol) and CuBr (10 mol %) were added. The reaction mixture was heated at 60 C until completion as indicated by TLC. Then the mixture was cooled down to room temperature and quenched with sat. NH4Cl solution (5 mL). The aqueous phase was extracted with EtOAc (3 x10 mL). The combined organic phases were dried (Na2SO4), and the solvent was removed under reduced pressure. The obtained crude product was purified by flash column chromatography.

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, 2-Iodo-5-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chang, Cai-Zhu; Xu, Wan; Zeng, Meng-Tian; Liu, Min; Liu, Xing; Zhu, Hui; Dong, Zhi-Bing; Synthetic Communications; vol. 47; 13; (2017); p. 1262 – 1267;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 31599-60-7, 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.

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: …

The synthetic route of 31599-60-7 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, 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 103962-05-6, name: 1-Iodo-4-(trifluoromethoxy)benzene

General procedure: A Schlenk tube was charged with a mixture of tetrahydroberberrubine (1, 228 mg,0.70 mmol), potassium carbonate (97 mg, 0.70 mmol), copper(I) iodide (13 mg,0.07 mmol), picolinic acid (17 mg, 0.14 mmol), aryl iodide (1.40 mmol, 2 equiv) andDMSO (6 mL) before it was evacuated and backfilled with N2 for three times. Thereaction mixture was stirred for 24 h at 100 C and the resulting mixture was subjectedto column chromatography (SiO2, CH2Cl2/MeOH 200:1-150:1) to give the respectiveproduct 2a-o as pale-yellow solids and 4 as yellow solid. Characterization data and theoriginal spectra are presented below.

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; Teng, Qiaoqiao; Zhu, Xinhui; Guo, Qianqian; Jiang, Weihua; Liu, Jiang; Meng, Qi; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1575 – 1580;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com