Month: November 2020

13194-68-8,Some common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-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.

In 10 ml of acetonitrile was dissolved 1.5 g (4 mmol) of N-(1,1-dimethyl-2-methylthioethyl)-3-iodophthalisoimide, and 0.89 g (3.8 mmol) of 4-iodo-2-methylaniline was added to the solution. After 10 minutes, the crystals precipitated were collected by filtration to obtain 1.94 g of the desired compound. Physical property: m.p. 155-157C. Yield: 84%.

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-2-methylaniline, its application will become more common.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; EP1389613; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

52548-14-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 52548-14-8 name is 2-Iodo-5-methylbenzoic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In the reactor,Add 250mL of acetone,Stirring,26.2 g of 2-iodo-5-methylbenzoic acid,Then 34.5 g of potassium carbonate was added,0.38 g copper iodide (Cul),1,2,3-triazole 7.6g.External temperature was raised to 70 C,During the heating process, a large amount of gas is generated,The reaction was refluxed for 5 hours.Then the reaction mixture was distilled under reduced pressure, the reaction system is more viscous, add 30mL of water, continue to reduce the steam distillation to no acetone (no acetone gas phase). 300mL of water was added to the residue after distillation, and 6mo 1 / L hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1-2, resulting in a khaki-colored suspension liquid. Stirred for 15 minutes, filtered, washed with water three times,Each 50mL. The resulting solid was dried at 70 C in vacuo to dryness,Have pale green solid 19.45g,For crude compound (1-1), the purity was 95.20%.With stirring, 7.5 kg of acetone, 0.94 kg of crude compound (1-1) and 0.194 kg of sodium hydroxide were added to the reaction kettle. Stirred at 20 C-30 C for 14 hours. Centrifugation, The filter cake was washed 3 times with acetone, each time 3kg. The resulting solid was transferred to the reaction kettle , 5.65 kg of water was added, 0.14 kg of diatomaceous earth was added and stirred for 1 hour. Filtration, the filtrate was transferred to the reaction kettle, hydrochloric acid was added dropwise to adjust the pH to 1-2, a large amount of white solid formed and stirred for 1 hour. Filtered, the filter cake was washed with water three times, each time 3kg. The resulting solid was dried at 60 C in vacuo to dryness, 0.71 kg white solid, represents Compound (I-1), purity 99.97%, Isomeric compound (1-2) less than 0.1%.

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; He Bifei; Fan Yuping; (6 pag.)CN104649983; (2018); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5100-98-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5100-98-1 name is 3-Chloro-2-iodotoluene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: For a typical reaction, a Vapourtec 2R+ Series was used as the platform with a Vapourtec Gas/Liquid Membrane Reactor to load the carbon monoxide. The HPLC pump were both set at 0.125 mL/min, temperature of the reactor at 110 ¡ãC, pressure of CO at 15 bar with a back pressure regulator of 250 psi (17.24 bar). The system was left running for 2 h to reach steady state after which time the flow streams were switched to pass from the loops where the substrates and catalysts were loaded. The first loop (5 mL) was filled with a solution of palladium acetate (20 mg, 0.08 mmol), triphenylphosphine (48 mg, 0.168 mmol) in 6 mL of 1,4-dioxane while the second loop (5 mL) was filled with a solution made from the ortho-substituted iodoarene substrate (1.68 mmol), triethylamine (0.272 g, 0.374 mL, 2.69 mmol) and water (0.505 g, 28 mmol) in 5.8 mL of 1,4-dioxane. An Omnifit? column filled with 1.71 cm3 (r = 0.33 cm, h = 5.00 cm) of cotton was positioned just before the back pressure regulator to trap any particulate matter formed to avoid blocking of the back pressure regulator. After the substrates were passed through the system, the outlet of the flow stream was directed into a receptacle where the excess carbon monoxide gas was vented off in the fume cupboard. The reaction mixture was then evaporated to dryness, ethyl acetate (25 mL) and sodium carbonate solution (2 M, 10 mL) were added and transferred to a separating funnel. After collecting the aqueous layer, the organic layer was extracted with sodium carbonate solution (2 M, 2 ¡Á 10 mL). The combined aqueous layers were acidified by the addition of 2 M HCl solution which was then extracted with ethyl acetate (3 x 25 mL). The organic layer was dried over sodium sulfate, and the solvent evaporated under vacuum to give the crude product as a solid. The crude product was then recrystallised from the appropriate solvent.

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

Reference:
Article; Mallia, Carl J.; Walter, Gary C.; Baxendale, Ian R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1503 – 1511;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1643-29-4, 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. 1643-29-4, name is 3-(4-Iodophenyl)propanoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

lntermediate-2; Methyl 3-(4-iodophenyl)propanoate.; Methanol (5 ml.) under nitrogen at O0C was added AcCI (0.4 ml_, 5.63 mmol). The reaction was stirred for 10 min before slow addition of 3-(4-iodophenyl)propanoic acid (498 mg, 1.80 mmol). The reaction was stirred for additional VA hour at room temperature, before the mixture was concentrated under vacuum, re-dissolved in MeOH and concentrated to give 512 mg (98%) of a pure white solid. Rf: 0.39 (EtOAc:hexanes, 1 :4); 1HNMR (CDCI3) delta 7.61-7.59 (m, 2H), 6.97- 6.94 (m, 2H), 3.66 (s, 3H), 2.92-2.87 (t, 2H, J = 7.5 Hz), 2.63-2.58 (t, 2H, J = 7.5 Hz); 13CNMR (CDCI3) delta 173.0, 140.1 , 137.5, 130.4, 91.4, 51.7, 35.4, 30.4; EI-MS m/z 290.0 (MH+).

The synthetic route of 3-(4-Iodophenyl)propanoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYDDANSK UNIVERSITET; ULVEN, Trond; CHRISTIANSEN, Elisabeth; WO2010/12650; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, A common compound: 116632-39-4, name is 5-Bromo-2-iodotoluene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a 20 mL vial with a stir bar was added aryl halide 1 (2.00 mmol), Pd(dba)2 (28.8 mg, 2.5 mol %), Xantphos (28.9 mg, 2.5 mol %). The vial was sealed with a Teflon-lined cap and THF (6.0 mL) was added. The mixture was vacuumed and backfilled with nitrogen (3¡Á). A solution of ethyl 2-bromozincacetate (2a) in THF (0.40 M, 6.0 mL, 1.2 equiv) filtered through a Target Nylon 0.45 mum filter (1.25-inch OD) was syringed in and the reaction mixture was then heated to 65 C and monitored by HPLC. Upon reaction completion based on HPLC analysis (?95% conversion unless the reaction was stalled), the mixture was cooled to room temperature and quenched with 1 M aq HCl (5.0 mL), followed by addition of brine (5.0 mL). The organic layer was separated and concentrated in vacuum. The residue was purified by silica gel column chromatography using gradient EtOAc in hexanes.

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, 5-Bromo-2-iodotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wong, Brian; Linghu, Xin; Crawford, James J.; Drobnick, Joy; Lee, Wendy; Zhang, Haiming; Tetrahedron; vol. 70; 7; (2014); p. 1508 – 1515;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 351003-36-6, name is 2-Fluoro-5-iodobenzonitrile, 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 351003-36-6, 351003-36-6

Step 2: lambda/-r3-(3-Cvano-4-fluorophenyl)prop-2-vti-l-yll-N-(2,4-dimethoxybenzyl)-lH-pyrrole-2- carboxamide (A2)To a solution of Al (1 eq) in a mixture of DMF and Et3N (1:1) was added 2-fluoro-5- iodobenzonitrile (2 eq), CuI (0.2 eq) and Pd(PPh3)4 (0.05 eq). The resulting mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc, washed with 0. IN HCl (2x) and then with brine; dried (Na2SO4) and concentrated. The resulting crude was purified by on silica gel eluting with EtO Ac/petrol ether to obtain the desired compound. MS (ES) C24H2OFN3O3 requires: 417, found: 418 (M+H)+. 1R NMR (400 MHz, DMSOd6) delta: 11.59 (IH, bs), 7.93 (IH, dd, J = 6.3, 2.0 Hz), 7.78-7.73 (IH, m), 7.53 (IH, t, J = 9.1 Hz), 7.13 (IH, d, J = 8.3 Hz), 6.93 (IH, s), 6.60 (IH, d, J = 2.3 Hz), 6.53 (IH, dd, J = 8.3, 2.3 Hz), 6.50-6.38 (IH, m), 6.10 (IH, s), 4.77 (2H, s), 4.50 (2H, s), 3.78 (3H, s), 3.76 (3H, s).

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-5-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/138355; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

13697-89-7, 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. 13697-89-7, name is 1,3-Difluoro-2-iodobenzene, A new synthetic method of this compound is introduced below.

B 5-Fluoro-1,4-dihydro-1,4-methano-naphthalene A solution of 2,6-difluoroiodobenzene (5.0 g, 20.8 mmol) and cyclopentadiene (2.07 g, 31.3 mmol) was stirred at 0 C. in P. ether (70 mL, 40-60 C.) under N2 and treated with n-BuLi (8.74 mL, 2.5M in hexanes, 21.8 mmol) dropwise over 10 minutes. The reaction was quenched after 15 minutes by addition of aqueous 1N HCl solution and the product was extracted with hexanes (3*50 mL). The combined organic layer was washed with H2O (50 mL), saturated aqueous NaCl solution (50 mL), dried (MgSO4), filtered and evaporated. Chromatography on Silica gel provided product as an oil (1.5 g, 45%). (TLC hexanes Rf 0.55). 1H NMR (400 MHz, CDCl3) delta 7.08 (ddd, J=7.0, 1.0, 0.8 Hz, 1H), 6.96 (ddd, J=8.5, 8.3, 7.0 Hz, 1H), 6.86 (br s, 2H), 6.72 (ddd, J=8.5, 8.3, 0.8 Hz, 1H), 4.25 (br s, 1H), 3.98 (br s, 1H), 2.36 (ddd, J=7.2, 1.7, 1.7 Hz, 1H), 2.30 (ddd, J=7.2, 1.7, 1.5 Hz, 1H). GCMS m/e 160 (M+).

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; Pfizer Inc; US6605610; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

112671-42-8,Some common heterocyclic compound, 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, molecular formula is C6H3BrINO2, 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.

Intermediate Ml-a (5. lg, 18.4 mmol) and 2_p_5_ nitrobenzene (15.3 g, 46.7 mmol), tert-butanol sodium (7. lg, 74.4 mmol), toluene 100 mL, nitrogen Protection, 0.3g Pd2 (dba) 3, tri-tert-butylphosphine (20ml, 10% toluene solution), start stirring, heat to 100 C reflux, reaction 12h, the reaction liquid is washed, the organic phase is concentrated, passed through the silica gel column, rinse The oil was petroleum ether: ethyl acetate = 50:1, and the eluent was concentrated to give intermediate Ml-b (9.2 g, yield: 7.39 %).

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

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Fan Hongtao; Zhang Yaguang; Zhang Xianghui; Ren Xueyan; (28 pag.)CN108341826; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

61203-48-3, The chemical industry reduces the impact on the environment during synthesis 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, I believe this compound will play a more active role in future production and life.

[C.] [N- (8-NITROQUINOLIN-4-YL)-N- (N, N-DIMETHYLAMINOETHYL)-2-IODO-5,] 6- dimethoxybenzamide (8a). Oxalyl chloride (762 mg, 6.0 mmol) was added to a solution of 3,4-dimethoxy-6-iodobenzoic acid (570 mg, 1.85 mmol) in anhydrous methylene chloride (20 mL), and the stirred mixture was refluxed for 3 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 20 mL of anhydrous methylene chloride, and this solution was added to a solution of 7a (400 mg, 1.54 mmol) and triethylamine (1.14 g, 11.3 mmol) in methylene chloride (20 mL), and the resulting mixture was stirred at reflux overnight. The reaction mix was cooled and washed with saturated sodium bicarbonate (3 x 75 mL), and extracted with 5 % aqueous [HC1] (4 x 100 mL). The combined aqueous extracts were basified with 30% [NAOH] and then extracted with chloroform (3 x 100 mL). Combined organic extracts were then dried [(MGS04)] and evaporated to give 722 mg of the amide, in 85 % yield [; IH] NMR [(CDC13)] 6 2.30 (s, 6H), 2.69 (m, 2H), 3.32 (s, 3H), 3.74 (s, 3H), 3.95 (m, 1H), 4.57 (m, 1H), 6.41 (s, 1H), 7.02 (s, 1H), 7.75 (m, 2H), 8.05 (d, 1H, [J=6.] 6), 8.44 (d, 1H, [J=8.] 4), 8.95 (d, 1H, [J=4.] 4) [; 13C NMR] [(CDC13)] [5] 45.4, 47.3, 55.7, 56.1, 56.5, 82.7, 110.7, 121.9, 123.3, 124.0, 126.1, 126.9, 127.2, 133.1, 140.9, 147.4, 148.4, 149.0, 150.1, 153.0, 169.9 ; IR (CHC13) 1362,1536, 1655.

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-4,5-dimethoxybenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

101335-11-9, Adding a certain compound to certain chemical reactions, such as: 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, 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 101335-11-9.

To a solution of 1 (30mg, 0.157mmol), 2 (81mg, 0.315mmol) and Cs2CO3 (256mg, 0.785mmol) in DMF (2mL) were added 1 mg of Pd(dba)2 and 1 mg of Xantphos. The suspension was degassed under vacuum and purged with N2 several times. The mixture was stirred at 120 C for 1hr. The reaction was quenched by adding water and extracted with EA. The combine organic phases were washed by water, brine, dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified by pre-TLC to obtain the title compound Compound 215 (6.15mg, yield: 12.3%). LCMS: m/z, 319.0(M+H)+; 1HNMR (d-CDCl3, 400MHz): delta 8.62-8.63 (m, 1H), 7.68-7.72 (m, 1H), 7.50-7.52 (m, 1H), 7.28-7.32 (m, 1H), 7.09-7.12 (m, 1H), 6.91-6.93 (m, 2H), 4.06-4.17 (m, 1H), 3.68-3.77 (m, 2H), 3.33-3.38 (m, 1H), 2.46-2.69 (m, 2H).

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-Chloro-4-fluoro-1-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com