Month: August 2021

These common heterocyclic compound, 2974-94-9, name is 1-Iodo-4-phenoxybenzene, 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. HPLC of Formula: C12H9IO

Example 9 1-(2-{[3-(4-Phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with 4-iodophenyl phenyl ether (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluding with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluding with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluding with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-{[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148 C. Analysis. Calculated for C27H22N4O2.(H2O)4/5: %C, 72.24; %H, 5.30; %N, 12.48. Found: %C, 71.82; %H, 4.85; %N, 12.35. 1H NMR (300 MHz, DMSO-d6) delta 8.18 (s, 1H), 8.12 (d, J=7.4 Hz, 1H), 7.62 (d, J=7.7 Hz, 1H), 7.41-7.47 (m, 3H), 7.18-7.27 (m, 4H), 7.06 (dd, J=7.6, 1.0 Hz, 2H), 6.90 (dd, J=6.7 Hz, 2H), 6.71 (s, 2H), 4.85 (t, J=5.1 Hz, 2H), 4.37 (s, 2H), 4.02 (t, J5.0 Hz, 2H); IR (KBr) 3444, 3070, 2928, 1500, 1230, cm-1; HRMS (EI) Calculated for C27H22N4O2 (M+) 434.1743, found 434.1748.

The synthetic route of 1-Iodo-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M Innovative Properties Company; US6677348; (2004); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 111771-08-5, The chemical industry reduces the impact on the environment during synthesis 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, I believe this compound will play a more active role in future production and life.

Step A: 2-Fluoro-6-iodo-benzoic acid methyl ester. To a 200 mL round- bottomed flask were added 2-fluoro-6-iodo-benzoic acid (7.5 g, 28.2 mmol), LiOH*H2O (1 .42 g, 33.8 mmol), and THF (100 mL). The resulting mixture was warmed to 50 C and stirred for 2 h. Dimethyl sulfate (4.03 mL, 42.3 mmol) was then added and the mixture was warmed to 65 C. After 2 h, the mixture was cooled to room temperature and NH4CI(aq) (50 mL, 13 wt% solution) was added. The two resulting layers were thoroughly mixed and then separated. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a light brown oil (7.79 g, 99% yield). 1H NMR (400 MHz, CDCIs): 7.68 – 7.60 (m, 1 H), 7.15 – 7.06 (m, 2H), 3.98 (s, 3H).

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-Fluoro-6-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13194-68-8, name is 4-Iodo-2-methylaniline, 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 13194-68-8, Formula: C7H8IN

Compound 4 (5.67 g, 21.5 mmol) and dibutylhydroxytoluene (10 mg, 45 mumol) were dissolved in a mixed solution of toluene (10 ml) and dimethyl acetamide (10 ml). Thionyl chloride (1.50 ml, 20.7 mmol) was added dropwise to the resulting solution under ice cooling, and the solution was stirred at room temperature for 4 hours. Furthermore, a dimethyl acetamide solution (10 ml) of 4-iodo-2-methylaniline (2.00 g, 8.58 mmol) was added dropwise to the resulting solution under ice cooling, and the solution was stirred at 80 C. for 2 hours. After cooling the solution to room temperature, 1 N hydrochloric acid was added to the solution, followed by extraction with ethyl acetate. The organic layer obtained by the extraction was washed once with aqueous sodium bicarbonate and once with saline, respectively, and sodium sulfate was added to the washed organic layer. The obtained organic layer was filtered to collect the filtrate, and then the solvent was distilled off from the filtrate under reduced pressure. The resulting residue was purified by flash column chromatography to obtain Compound 8 (3.17 g) as a white solid.

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

Reference:
Patent; FUJIFILM Corporation; FUKUSHIMA, Yuki; GOTO, Ryoji; US2019/177268; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103962-05-6,Some common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H4F3IO, 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 250 mL reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 hours (h). The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite®. The Celite® was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent to yield the title compound (3.78 g, 73percent): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307 ([M]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; WHITEKER, Gregory T.; US2014/275560; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, molecular formula is C6H4F2IN, 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. name: 4,5-Difluoro-2-iodoaniline

A dark violet solution of 2-iodo-4,5-difluoroaniline (1a) (148 mg, 0.582 mmol), gold complex [AuPPh3NN] 2 (308 mg, 0.5 mmol),[Pd(PPh3)4] (52 mg, 0.045 mmol) in 7 ml of acetonitrile were stirred in an argon atmosphere at 60-65 C for 1 h. The reaction mixture was evaporated. The product was isolated by column chromatography on SiO2, using a mixture of methylenechloride with ethylacetate (3:1) as the eluent. Yield: 71 mg (50%), dark purple crystals, Tmelt = 140-141 C. UV spectrum(CH2Cl2), lambdamax, nm (lgepsilon): 240 (4.00), 260 (3.79), 346 (4.07), 578 (2.88). IR spectrum (KBr), v , cm-1: 3357, 3168 (NH2), 2996(C-H), 1646, 1592, 1502, 1355, 1143, 873, 788. Found, %: 55.07, 5.63, N 14.64. Calculated, %: 54.93, 5.63, N14.78.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 847685-01-2, its application will become more common.

Reference:
Article; Tretyakov; Makhneva; Politanskaya; Bagryanskaya, I. Yu.; Stass; Journal of Structural Chemistry; vol. 59; 3; (2018); p. 689 – 696; Zh. Strukt. Kim.; vol. 59; 3; (2018); p. 712 – 719,8;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 101335-11-9, 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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: (E)-4-(2-(2-Chloro-4-fluorophenyl)-l-(4-(thiazol-5-yl)phenyl)but-l-en-l- yl)benzaldehyde[00394] A mixture of (Z)-4-(2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-(4-(thiazol-5- yl)phenyl)but-l-en-l-yl)benzaldehyde (99 mg, 0.22 mmol), 2-chloro-4-fluoro-l-iodobenzene (114 mg, 0.44 mmol), Pd(PPh3)2Cl2(15 mg, 0.022 mmol), and KOH (6M, 0.2 mL, 1.32 mmol) in 1,4-dioxane (2.2 mL) was heated to 90C overnight. After cooling, ethyl acetate and brine were added to the reaction mixture and the two layers were separated. The organic layer was washed with more brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel to afford 68 mg of a mixture of the title compound (major) and the undesired regioisomer (minor). 1H NMR (400 MHz, DMSO-d6) of major: delta 9.84 (s, 1H), 9.11 (s, 1H), 8.35 (s, 1H), 7.75 (d, 2H), 7.64 (d, 2H), 7.40-7.33 (m, 4H), 7.17 (m, 3H), 2.45 (q, 2H), 0.93 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluoro-1-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SERAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; GOVEK, Steven, P.; KAHRAMAN, Mehmet; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2014/151899; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 112671-42-8, name is 4-Bromo-1-iodo-2-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 112671-42-8, name: 4-Bromo-1-iodo-2-nitrobenzene

Intermediate M1 – a (5.1 g, 18.4 mmol) with 2 – iodo -5 – bromo nitrobenzene (15.3 g, 46.7 mmol), sodium tertiary butyl alcohol (7.1 g, 74.4 mmol), toluene 100 ml, nitrogen protection, 0.3 gPd2(Dba)3, Tri-[…] (20 ml, 10% toluene solution), open mixing, heating to 100 C reflux, the reaction 12 h, washing the reaction solution, the organic phase is concentrated, over silica gel column, eluent ethyl acetate is petroleum ether=50 1, concentrated eluent, get midbody M1 – b (9.2 g, yield 73.9%).

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-Bromo-1-iodo-2-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Fan Hongtao; Xing Qifeng; Zhang Wei; Zhang Xianghui; (25 pag.)CN107880051; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, 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 216393-67-8, HPLC of Formula: C6H4ClFIN

A mixture of Int-172-27 (5 g , 18.4 mmol), 23 (9.9 mL, 110.5 mmol), K2CO3 (3.05 g, 22.1 mmol), DPPP (366 mg, 0.92 mmol) and Pd(OAc)2 (41 mg, 0.18 mmol) in 60 mL H2O/toluene (9:1) was heated at 90oC for 24h. After the mixture was cooled to room temperature, concentrated HCl (14 mL) was slowly added and the mixture was stirred at room temperature for 1h. The product was extracted with EtOAc (3X). The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The product was purified by column chromatography using hexanes/EtOAc (0 to 20% EtOAc in hexanes) and obtained as a pale brown solid (1.3 g) in 37% yield. LCMS: (M+1) m/z = 188.

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:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BLACKTHORN THERAPEUTICS, INC.; ROBERTS, Edward; GUERRERO, Miguel A.; URBANO, Mariangela; ROSEN, Hugh; JONES, Rob; LAXAMANA, Candace Mae; ZHAO, Xianrui; TURTLE, Eric Douglas; (331 pag.)WO2018/170492; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 21740-00-1, 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 21740-00-1 as follows.

General procedure: A mixture of 2-iodobenzoic 1a (0.2 mmol), acetylacetone 2a (0.4 mmol), and Cs2CO3 (65.2 mg, 0.20 mmol) in CH3CN was stirred at 100 C. When the reaction was considered complete as determined by TLC analysis, the reaction was allowed to cool to room temperature and quenched by water, and the mixture was extracted with CH2Cl2. The combined organic extracts were washed with water and saturated brine. The organic layers were dried over Na2SO4, filtered. Solvents were evaporated under reduced pressure. The residue was purified by chromatography on silica gel to afford isocoumarins derivatives and isoquinolone derivatives.

According to the analysis of related databases, 21740-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Lei; Hu, Jie; Wang, Xiang-Chuan; Zhong, Mei-Jin; Liu, Xue-Yuan; Yang, Shang-Dong; Liang, Yong-Min; Tetrahedron; vol. 68; 27-28; (2012); p. 5391 – 5395;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 31599-61-8,Some common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, molecular formula is C8H9I, 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.

0.288 mol of 3,4-dimethyl iodobenzene, 0.24 mol of carbazole, 0.02 mol of phenanthroline, 0.02 mol of cuprous iodide,Cesium carbonate 0.384 mol was charged into a 1000 ml three-necked flask, dissolved in 300 ml of DMF,Vacuum – nitrogen three times, the temperature to 152 C, the reaction overnight. The reaction solution was passed through a silica funnel,Rinse with methylene chloride to no product dissolution;Spin to about 400ml with 500ml water, liquid, take dichloromethane phase, washed with water three times; spin dry,Add 100ml dissolved,Add 500ml of ethanol to a large amount of solid precipitation, filtration, vacuum drying at 55 .To give 0.2136 mol of 9- (3,4-dimethylbenzene) -9H-carbazole in 89% yield

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

Reference:
Patent; Jilin Optical and Electronic Materials Co., Ltd.; Gao, Chunji; Wang, Yongguang; Li, Wenjun; Bi, Yan; (17 pag.)CN104650044; (2017); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com