Author: Jessica.F

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

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

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

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 17024-12-3 as follows. HPLC of Formula: C14H9I

Mixed under argon flow were 100 g of 1-aminonaphthalene (manufactured by Aldrich Co., Ltd.), 255 g of 9-iodophenanthrene, 204 g of anhydrous potassium carbonate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.7 g of copper powder (manufactured by Hiroshima Wako Co., Ltd.) and 750 ml of decalin, and they were reacted at 190C for 3 days. After cooling, 2 liter of toluene was added thereto to filter an insoluble matter. The matter filtered was dissolved in 4.5 liter of chloroform to filter off an insoluble matter, and then the filtrate was treated with activated carbon and concentrated under reduced pressure. Acetone 3 litter was added when the solution became slurry in the middle of concentration, and crystal deposited was filtered and refined through a column. Mixed under argon flow were the powder obtained, 200 g of 4-bromoiodobenzene (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 204 g of anhydrous potassium carbonate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.7 g of copper powder (manufactured by Hiroshima Wako Co., Ltd.) and 750 ml of decalin, and they were reacted at 190C for 3 days. After cooling, 2 liter of toluene was added thereto to filter an insoluble matter. The matter filtered was dissolved in 4.5 liter of chloroform to filter off an insoluble matter, and then the filtrate was treated with activated carbon and concentrated under reduced pressure. Acetone 3 litter was added when the solution became slurry in the middle of concentration, and crystal deposited was filtered. This was refined through a column and dissolved in toluene, and hexane was added thereto to reprecipitate crystal. It was filtered and then dried to obtain 64 g of N-(4-bromophenyl)-N-(phenantho-9-yl)-1-naphthylamine (B8).

According to the analysis of related databases, 17024-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1559706; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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. Computed Properties of C2H2IN

The compound obtained in Example 64 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and the residue was treated in water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of regioisomers as yellow oil. These two regioisomers (4.16 g, 80%) were used in the next reaction step without separation.Example 65-2Preparation of 4-(2-chloropyridin-5-yl)-5-(3-methoxy-5-methylphenyl)-pyrazol-1-yl)acetonitrile1H NMR (CDCl3) delta 2.28 (s, 3H), 3.66 (s, 3H), 5.16 (s, 2H), 6.71 (s, 2H), 6.84 (s, 1H), 7.24 (d, J=8.3 Hz, 1H), 7.49 (dd, J=2.3, 5.9 Hz, 1H), 7.70 (s, 1H, 8.32 (s, 1H); 13C NMR (CDCl3) delta 21.57, 39.89, 55.23, 110.80, 113.76, 115.28, 117.76, 121.47, 124.02, 127.24, 129.92, 132.57, 138.58, 140.12, 148.71, 149.92, 151.17, 159.69, 162.33.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 65 (0.3 g, 0.89 mmol), 3-pyridineboronic acid (0.13 g, 1.07 mmol), dichlorobis(triphenylphosphine)palladium (II) (32 mg, 0.05 mmol) and potassium carbonate (0.13 g, 0.89 mmol). The reaction system was purged with nitrogen gas for 10 min, and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:3, v/v): (87 mg); m.p. 64-65 C.; in NMR (CDCl3) delta 2.37 (s, 3H), 3.79 (s, 3H), 4.94 (s, 2H), 6.71 (s, 1H), 6.77 (s, 1H), 6.88 (s, 1H), 7.36-7.40 (m, 1H), 7.60-7.67 (m, 2H), 7.92 (s, 1H), 8.27 (d, J=7.7 Hz, 1H), 8.60-8.62 (m, 2H), 9.15 (s, 1H); 13C NMR (CDCl3) delta 21.60, 37.81, 55.41, 112.42, 114.14, 116.71, 118.30, 120.26, 122.69, 123.62, 127.25, 128.99, 134.09, 134.43, 135.01, 139.48, 141.21, 141.39, 147.98, 148.25, 149.80, 152.64, 160.40.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
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 23399-70-4 as follows. COA of Formula: C7H6ClI

Step 2: At O0C5 a solution of 4-chloro-l-iodo-2-methylbenzene (642 mg, 2.53 mmol) in 5mL of pentane was treated with t-BuLi (1.68 mL of 1.7 M in pentane solution, 2.86 mmol) slowly, and stirred for 30 min. The resulting yellow mixture was cooled to – 60 0C, and a solution of N-methoxy-N-methyl-l-(trifluoroinethyl)cyclopropanecarboxamide (346 mg, 1.75 mmol) in 3.0 mL of THF was added via syringe. The reaction mixture was slowly warmed to RT in 1 h, then partitioned between a mixture of sat. ammonium chloride and EtOAc. The organic layer was separated, dried and concentrated. Purification of the residue on the ISCO (12 g column, 0-10% EtOAc:Hexanes) provided the title compound (384 mg, 83%) as a colorless amorphous solid. MS (ESI3 pos. ion) m/z: 263.1 (M+l).

According to the analysis of related databases, 23399-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; TASKER, Andrew; ZHANG, Dawei; WO2008/30466; (2008); 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. 627-32-7, name is 3-Iodo-1-propanol belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3-Iodo-1-propanol

D: 3-(4-Bromo-2-(trifluoromethyl)-phenoxy)propan-1-ol3-Iodopropanol (11.23 g) was added to a mixture of 4-bromo-2-(trifluoromethyl)-phenol (15 g) and potassium carbonate (172 g) in acetonitrile (150 ml). The above mixture was refluxed for 4 hours then diluted with ethyl acetate (500 ml) and water (300 ml). Organic layer was seperated, dried over magnesium sulphate, solvent removed under reduced pressure to give expected product clean enough for use at the next step (18.6 g). 1H NMR (CDCl3) delta: 7.67 (d, 1H), 7.58 (dd, 1H), 6.90 (dd, 1H), 4.18 (t, 2H), 3.87 (q, 2H), 2.07 (tt, 2H).

The synthetic route of 627-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. Organon; US2010/184761; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 56404-21-8, name is 1-Iodo-2,4-dimethyl-3-nitrobenzene, 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 56404-21-8, Application In Synthesis of 1-Iodo-2,4-dimethyl-3-nitrobenzene

A three-necked flask equipped with a thermometer, a gas inlet, and a magnetic stirring bar was charged under argon with MnBr2 (320mg, 1.5mmol) in DMPU (25ml). CuCl (85mg, lmmol), ethyl 4-bromobutyrate (5.85g, 30mmol) and Et2Zn (2.7ml, 27mmol) were successively added. The reaction mixture turned dark red and was stirred for 4 h at 25 0C. After cooling to -30 0C, a solution of Cl2Pd(dppf) (0.925g, lOmmol) and 2,4-dimethyl-3-nitroiodobenzene (6.93g, 25mmol) in anhydrous THF (25ml) was slowly added. The reaction mixture was warmed to 25 C for 30 min and was then stirred at 65 C overnight and quenched with an aqueous 2N HCl solution (100ml). This mixture was extracted with CH2Cl2 three times, and the organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the crude residue obtained was purified by Biotage (hexane/EtOAc, 0-30%, 40min) to give 4.5g of yellow oily products (68 %). 1H-NMR delta (CDCl3, 300MHz): 7.13 (d, J=7.8Hz, IH), 7.03 (d, J=7.8Hz, IH), 4.12 (q, J=7.2Hz, 2H), 2.64 (t, J=7.8Hz, 2H), 2.34 (t, J=7.8Hz, 2H), 2.23 (s, 3H), 2.20 (s, 3H), 1.86 (m, J=7.8Hz, 2H), 1.24 (t, J=7.8Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Iodo-2,4-dimethyl-3-nitrobenzene, and friends who are interested can also refer to it.

Reference:
Patent; VALEANT PHARMACEUTICALS INTERNATIONAL; WO2008/66900; (2008); A1;,
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. 74534-15-9, name is 1-Chloro-2-iodo-4-nitrobenzene, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

Iron (5 eq, 1.9 g) was added to a solution of 1-chloro-2-iodo-4-nitro-benzene (1eq, 1.95 g) in acetic acid (28 mL, 0.25M). The reaction was stirred at70C for 1 h then cooled to room temperature and filtered through celite. The crudereaction mixture was extracted with a solution of saturated ammonium chloride andethyl acetate, dried with magnesium sulfate, filtered and concentrated under vacuum toafford crude 4-chloro-3-iodo-aniline as a red oil, which was used in the next step withoutpurification.

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; Khojasteh, S. Cyrus; Yue, Qin; Ma, Shuguang; Castanedo, Georgette; Chen, Jacob Z.; Lyssikatos, Joseph; Mulder, Teresa; Takahashi, Ryan; Ly, Justin; Messick, Kirsten; Jia, Wei; Liu, Lichuan; Hop, Cornelis E. C. A.; Wong, Harvey; Drug Metabolism and Disposition; vol. 42; 3; (2014); p. 343 – 351;,
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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Iodoacetonitrile

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (320 mg, 0.95 mmol), 3-acetylphenyl boronic acid (0.19 g, 1.13 mmol), thchlorobis(triphenylphosphine)palladium (II) (33 mg, 0.05 mmol) and potassium carbonate (131 mg, 0.95 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:2, v/v): (197 mg, 79%); m.p. 73-74 C.; 1H NMR (CDCl3) delta 2.27 (s, 3H), 2.60 (s, 3H), 3.67 (s, 3H), 5.19 (s, 2H), 6.76 (s, 1H), 6.80 (s, 1H), 6.91 (s, 1H), 7.13 (s, 1H), 7.49 (bs, 1H), 7.64 (s, 1H), 7.85 (s, 1H), 7.95 (d, J=5.4 Hz, 1H), 8.04 (d, J=5.7 Hz, 1H), 8.39 (s, 1H), 8.56 (s, 1H); 13C NMR (CDCl3) delta 21.51, 26.78, 39.89, 55.23, 111.03, 113.93, 115.51, 119.76, 119.90, 121.63, 121.77, 126.71, 128.60, 128.76, 129.11, 130.54, 131.45, 132.06, 132.92, 137.52, 139.61, 140.00, 141.09, 149.91, 151.38, 156.47, 159.69, 198.16.

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; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com