Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 188815-32-9, name is 3-Bromo-5-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 188815-32-9, Safety of 3-Bromo-5-iodobenzoic acid

To a solution of 3-bromo-5-iodobenzoic acid (53, 500 mg, 1.53 mmol) in methanol (7.5 mL) was added dropwise thionyl chloride (1.1 mL, 2.18 g, 18.35 mmol) at 0 C, and then this reaction mixture was stirred at room temperature for 15 h. After being neutralized with saturated NaHCCb solution on the ice bath, the mixture was extracted with ethyl acetate (20 mL x2). The combined organic layer was washed with brine, dried over MgS04, filtered and evaporated under reduced pressure to afford compound 54 (498 mg, 96%) as a white solid; NMR (400 MHz, CDCb) d 8.32 (t, J =1.40 Hz, 1H), 8.15 (t, J =1.58 Hz, 1H), 8.06 (t, J =1.64 Hz, 1H), 3.95 (s, 3H); MS (ESI, m/z) 340.9, 342.9 [M+l]+; ESI-HRMS calcd. m/z for C8H702I79Br 340.8674, found 340.8672 [M+l]+.

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 UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; JACOBSON, Kenneth A.; YU, Jinha; CIANCETTA, Antonella; WEN, Zhiwei; JUNG, Young-Hwan; (124 pag.)WO2019/157417; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 146137-72-6, 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. 146137-72-6, name is 2-Fluoro-6-iodobenzaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 3-Iodo-1H-pyrazole-4-carbonitrile (3.62 g, 16.5 mmol) was taken up in dry tetrahydrofuran (67 ml) under nitrogen atmosphere. Sodium hydride (992 mg, 24.8 mmol, 60% in oil) was added in one portion and the mixture was placed in a heated (50 C.) sonication bath for 50 minutes. To this mixture was added 2-fluoro-6-iodobenzaldehyde (5.37 g, 21.5 mmol) and the mixture was placed in an oil bath heated to 60-65 C. After 2 hours stirring additional 2-fluoro-6-iodobenzaldehyde (350 mg, 1.4 mmol) was added and the material was stirred for 1 more hour. The flask was cooled to ambient and close to 90% of the solvent was stripped (rotary evaporator). Diethyl ether (30 ml) and water (50 ml) were added and the mixture was vigorously stirred for 30 minutes. The precipitated product was collected by filtration, rinsing well with diethyl ether and water, and drying in a vacuum oven to provide a light tan powder (4.78 g). This solid product was taken up in a solution of 2% methanol in dichloromethane (about 60 ml, heat to dissolve) and transferred to a reparatory funnel. Water (60 ml) was added and the material was shaken and the organic phase collected. This was dried with magnesium sulfate, filtered and stripped to provide the desired 1-(2-formyl-3-iodo-phenyl)-3-iodo-1H-pyrazole-4-carbonitrile as a light yellow powder (3.973 g). LC/MS calc’d for C11H5I2N3O (m/e) 448.99, obs’d 450 (M+H, ES+).

The chemical industry reduces the impact on the environment during synthesis 2-Fluoro-6-iodobenzaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Billedeau, Roland Joseph; Kondru, Rama K.; Lopez-Tapia, Francisco Javier; Lou, Yan; Owens, Timothy D.; Qian, Yimin; So, Sung-Sau; Thakkar, Kshitij C.; Wanner, Jutta; US2012/295885; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 13421-13-1, name is 4-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, 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. Safety of 4-Chloro-2-iodobenzoic acid

General procedure: To an oven dried three neck RB containing 2-Iodobenzoic acid (1) (2mmol), benzyl amine (2) (4mmol) and CuI(0.4mmol) in DMSO(3ml) was added 0.55g of K2CO3. Then, the reaction mixture was allowed to stir at 90C under air atmosphere for 12h.The completion of the reaction was monitored by TLC. After being cooled at room temperature the reaction mixture was poured in to ice cooled water and extracted with ethyl acetate two times. The combined organic layer was washed with brine and then dried over anhydrous Na2SO4. The solvent was evaporated and the crude product was purified by column chromatography (hexane(80)/ ethyl acetate (20)) on silica gel to afford 2-phenyl-4H-benzo[d][1,3]oxazine-4-one.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13421-13-1, its application will become more common.

Reference:
Article; Munusamy, Sathishkumar; Venkatesan, Sathesh; Sathiyanarayanan, Kulathu Iyer; Tetrahedron Letters; vol. 56; 1; (2015); p. 203 – 205;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19094-56-5, name is 2-Chloro-5-iodobenzoic acid, 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. name: 2-Chloro-5-iodobenzoic acid

Example 3; 4′-Chloro-3′-[[(cyclohexylmethyl)amino]carbonyl]-[l,l’-biphenyl]-2-carboxylic acid; EPO a) 2-Chloro-5-iodo-benzoic acid, 1,1-dimethylethyl ester; iV,iV-Dimethylformamide (1 drop) and oxalyl chloride (4.8 mL) were added to a stirred solution of 2-chloro-5-iodobenzoic acid (5 g) in dichloromethane (20 mL) at 0 C. The reaction was allowed to warm to room temperature, stirred under nitrogen for 2 hours, and then evaporated to dryness. The residue was dissolved in tetrahydrofuran (20 mL) and cooled to 0 0C. Potassium terf-butoxide (22 mL, 1 M solution in tetrahydrofuran) was added over 10 minutes. The reaction was allowed to warm to room temperature and stirred under nitrogen for 2 hours then poured into saturated aqueous sodium bicarbonate (50 mL). The layers were separated and the aqueous was extracted with diethyl ether (50 mL). The combined organics were dried, filtered and evaporated to afford the sub-title compound as an oil (5.7 g).1HNMR (400 MHz, d6-DMSO) delta 7.99 (IH, d), 7.87 (IH5 dd), 7.34 (IH, d), 1.54 (9H, s).

The synthetic route of 19094-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/80884; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 3930-83-4, name is 2-Iodobenzamide, 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 3930-83-4, Recommanded Product: 2-Iodobenzamide

General procedure: To a solution of 2-iodobenzamide (3) or 2-bromonicotinamide (6) (2.0 mmol) in DMSO (3 mL), was added aldehyde (2.2 mmol), NaN3 (260 mg, 4.0 mmol), CuBr (29 mg, 0.2 mmol), and l-proline (46 mg, 0.4 mmol). The reaction mixture was stirred at 80 C under air. After disappearance of the reactant (monitored by TLC), water (30 mL) was added to the mixture, and then extracted with ethyl acetate (15 mL) for three times. The extraction was washed with saturated NaCl solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (10:1 to 3:1) as the eluent to give the desired products 5 or 7.

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; Li, Ting; Chen, Minglu; Yang, Lei; Xiong, Zhengxin; Wang, Yongwei; Li, Fei; Chen, Dongyin; Tetrahedron; vol. 72; 6; (2016); p. 868 – 874;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13194-69-9, name is 2-Iodo-5-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 13194-69-9, Recommanded Product: 2-Iodo-5-methylaniline

The corresponding imidazopyridine compound (0.2 mmol) and cuprous iodide (0.02 mmol) were sequentially added to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.2-iodo-5-methylaniline (0.5 mmol),1,10-azaphenanthrene (0.06 mmol), DBU (0.8 mmol),Carbon disulfide (0.4 mmol) and toluene (2.0 mL) were added by syringe under oxygen.The reaction tube was placed in a 120 C oil bath and stirred for 7 hours. The resulting solution was cooled to room temperature, and 2 mL of deionized water was added to the reaction mixture, and the mixture was uniformly mixed.Each time, 3 mL of ethyl acetate was used as an extractant to perform a liquid separation extraction operation.The crude product is extracted from the reaction liquid, and the extract is combined, and the solvent is removed by a rotary evaporator; the residue is purified by a silica gel column (silica gel size: 200 mesh to 300 mesh,The eluent is petroleum ether/ethyl acetate (6:1 v/v)).The target product was obtained in 64.5 mg, yield 80%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-5-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 60577-34-6,Some common heterocyclic compound, 60577-34-6, name is 4-Iodo-N-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.

Part D: The product obtained above was dissolved in dichloromethane (100 mL), to which DIEA (12 mL) and chloroacetyl chloride (12 mL) were slowly added at 0 C. The reaction was stirred from 0 C. to rt for 4 hours, washed with 1.0 N HCl (2*) and brine, and dried over magnesium sulfate. After solvent removal, the crude product was purified by chromatography using ethyl acetate/hexane as eluent (2:8 to 4:6 ethyl acetate:hexane) to give the desired 2-chloro-N-(4-iodo-phenyl)-N-methyl-acetamide as a brown solid. MS found: (M+1)+=310.23.

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-N-methylaniline, its application will become more common.

Reference:
Patent; Smallheer, Joanne M.; Pinto, Donald J.; Wang, Shuaige; Qiao, Jennifer X.; Han, Wei; Hu, Zilun; US2004/6062; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 791642-68-7,Some common heterocyclic compound, 791642-68-7, name is 4-Bromo-1-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.

(Reference Example 4) 1-(4′-bromo-2′-methoxy-[1,1′-biphenyl]-4-yl)cyclopropanecarboxylic acid ethyl ester A 1,4-dioxane (15 ml)-water (10 ml) solution of 1.2 g (3.8 mmol) of 4-bromo-1-iodo-2-methoxybenzene synthesized in analogy to Reference Example 3, 1.1 g (3.5 mmol) of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylic acid ethyl ester (synthesized in accordance with the process described in ) and 1.1 g (10 mmol) of sodium carbonate was degassed and was purged with nitrogen. Next, 0.10 g (0.12 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride methylene chloride adduct was added. The mixture was stirred in a nitrogen atmosphere for 1.5 hours while performing heating at 80C. After the completion of the reaction, water was added to the reaction mixture liquid, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent: hexane:ethyl acetate = 94:6 to 75:25 (V/V)), and the fraction containing the target compound was concentrated under reduced pressure and was dried by vacuum heating to give the title compound weighing 0.72 g (1.9 mmol, yield 55%) as a white solid. Mass spectrum (EI, m/z): 374 [M]+. 1H-NMR spectrum (400MHz, CDCl3) delta: 7.45-7.41 (2H, m), 7.39-7.35 (2H, m), 7.19 (1H, d, J = 8.0 Hz), 7.15 (1H, dd, J = 8.0, 1.8 Hz), 7.10 (1H, d, J = 1.8 Hz), 4.12 (2H, q, J = 7.1 Hz), 3.81 (3H, s), 1.61 (2H, dd, J = 7.0, 4.0 Hz), 1.22 (2H, dd, J = 7.0, 4.0 Hz), 1.19 (3H, t, J = 7.1 Hz).

The synthetic route of 791642-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE Industries, Ltd.; IWASE, Noriaki; NISHIDA, Hiroshi; OKUDO, Makoto; ITO, Masaaki; KONO, Shigeyuki; MATOYAMA, Masaaki; USHIYAMA, Shigeru; OKANARI, Eiji; MATSUNAGA, Hirofumi; NISHIKAWA, Kenji; KIMURA, Tomio; (54 pag.)EP3162801; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 401-81-0, A common heterocyclic compound, 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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: 4-Iodoanisole (0.813 mmol, 200 mg), bis(pinacolato)diboron (1.219 mmol, 309 mg) were dissolved in 3 mL of dmf followed by copper ferrite nanoparticles (5mol% with respect to 4-iodoanisole) and potassiumtert-butoxide (1.219 mmol, 137 mg) were added to a 10 mLcapped vial and stirred at RT for time indicated. After stirring, the mixture was diluted with diethyl ether and filtered through celite bed. The filtrate was extracted with water (3 times) and the organic phase was dried over anhydrous MgSO4. The crude product was subjected to analyze by GC-MS. The conversion yield is accurately measured based on the consumption of 4-iodoanisole and the side product formed due to protodeiodination.

The synthetic route of 401-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohan, Balaji; Kang, Hyuntae; Park, Kang Hyun; Catalysis Communications; vol. 85; (2016); p. 61 – 65;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 138385-59-8, A common heterocyclic compound, 138385-59-8, name is 4-Iodo-2,6-dimethylaniline hydrochloride, molecular formula is C8H11ClIN, 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.

Z) -Methyl 3- (4-amino-3, 5-dimethylphenyl)-2- (benzyloxycarbonyl) acrylate; A 2 L round bottom flask, was charged with 4-iodo-2,6- dimethylbenzenamine hydrochloride salt (55 g, 194 mmol), methyl 2- (benzyloxycarbonyl) acrylate (59.2 g, 252 mmol), tetrabutylammonium chloride (59.2 g, 213 mmol), palladium acetate (4.34 g, 19.4 mmol), and tetrahydrofuran (1.2 L, degassed by a flow of nitrogen for 30 min). The mixture was stirred to form a suspension and degassed by a flow of nitrogen for 30 min. Triethylamine (110 mL, 789 mmol) was then added and the resulting mixture was heated at reflux for 3h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite and washed twice with tetrahydrofuran (2 x 100 mL). The solvents were removed and the residue was dissolved in methylene chloride which was extracted with water (3X), brine (2X), dried over sodium sulfate and concentrated. Column chromatography on silica gel using 1: 9 ethyl acetate/methylene chloride as eluent afforded a tan solid, which was recrystalized from methanol (210 mL) and water (100 mL). After filtration, the solid was washed with ice cold 1: 1 methanol/water mixture and then dried under high vacuum overnight at room temperature to afford the title compound (58.0 g, 65%) as a light tan solid. NMR shows a 2.7 : 1 ratio of Z and E isomers which were not separated.’H-NMR (DMSO-d6) 8 8.79 (s, 0.73H), 8.51 (s, 0.27 H), 7.40-7. 21 (m, 8H), 5.24 (s, 2H), 5.13 (s, 1.46 H), 5.00 (s, 0.54 H), 3.68 (s, 2.2 H), 3.61 (s, 0.8 H), 2.05 (s, 6H) ;’3C-NMR (DMSO-d6) 8166. 0,154. 7,146. 9, 137.2, 135.8, 130.9, 128.3, 127. 7, 127. 3,120. 3,120. 0,119. 4,65. 3,51. 7,17. 8.

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; BRISTOL-MYERS SQUIBB COMPANY; WO2005/56550; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com