Month: February 2021

Application of 31827-94-8, 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. 31827-94-8 name is 2-Bromo-1-(4-iodophenyl)ethanone, 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.

This was a 2-step reaction process. To a solution of (5)-5-(tert-butoxycarbonyl)-5- azaspiro[2.4]heptane-6-carboxylic acid (1.122 kg, 4.65 mol, 1 equiv.) in anhydrous MeCN (10 L) was charged 4′-iodo bromoacetophenone (1.56 kg, 4.80 mol, 1.032 equiv.). The resulting suspension was charged DIPEA (1.215 L, 1.5 equiv.) at the ambient temperature over the period of about 15 min. Upon the completion of the DIPEA addition, the reaction was slightly exothermic (the internal temperature increased up to 25C) and the reaction mass became a clear solution. The reaction was complete within a couple of hours as indicated by HPLC (99+% conversion). It was rotavapped down, solvent swapped to EtOAc (11 L), subsequently washed with water (3 L), then sodium bicarbonate solution (3 L), and finally with brine (2 L). Upon drying over Na2S04, it was rotavapped to dryness and chased with toluene (4 L x 2) to dryness and finally charged toluene (8 L) to give a solution of the coupled intermediate in toluene (about 86% HPLC purity). ESI MS m/z (M+H)+486.13.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-(4-iodophenyl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; TANG, Datong; XU, Guoyou; PENG, Xiaowen; YING, Lu; WANG, Ce; CAO, Hui; LONG, Jiang; KIM, In, Jong; WANG, Guoqiang; QIU, Yao-ling; OR, Yat, Sun; WO2013/59281; (2013); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 68507-19-7, These common heterocyclic compound, 68507-19-7, name is 3-Iodo-4-methoxybenzoic acid, 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.

Standard conditions: iodobenzoic acid (0.55 mmol) , HP(0)Ph2, base, Pd/C, 0 (10 mL) , conventional heating, 100 C, 1 h. b 70 C.

Statistics shows that 3-Iodo-4-methoxybenzoic acid is playing an increasingly important role. we look forward to future research findings about 68507-19-7.

Reference:
Patent; PAUL SCHERRER INSTITUT; RANOCCHIARI, Marco; RUMMELT, Stephan; VAN BOKHOVEN, Jeroen A.; WO2013/117440; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 41860-64-4,Some common heterocyclic compound, 41860-64-4, name is 4-Fluoro-2-iodo-1-nitrobenzene, molecular formula is C6H3FINO2, 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.

A. 5-fluoro-4′-methylsulfinyl-2-nitrobiphenyl sulfide p-Methylsulfinylthiophenol 0.2 mole) is dissolved in dry tetrahydrofuran (100 ml.) and sodium hydride (50% dispersion in mineral oil, 0.2 mole) is added over 30 minutes. The solution is evaporated to dryness and the residue rinsed well with n-hexane. The powdered salt is stirred under N2 at reflux with 4-fluoro-2-iodonitrobenzene (0.2 mole) in dry dimethylformamide for 16 hours, evaporated to dryness and extracted into chloroform (3 * 200 ml.). The organics are washed with water (2 * 100 ml.), separated and dried (MgSO4). The solution is filtered, evaporated to dryness and put on a column of silica-gel (Baker 2 in. * 2 ft.) and various fractions eluted with portions of benzene-n-hexane. In this way, pure 5-fluoro-4′-methylsulfinyl-2-nitrobiphenyl sulfide is obtained.

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

Reference:
Patent; Merck & Co., Inc.; US3954852; (1976); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 2043-57-4, 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 2043-57-4 as follows.

General procedure: Under an argon atmosphere, fluorinated iodide (11-13) (1.19 mmol, 1 equiv) and NaN3 (3.57 mmol, 3equiv) were dissolved in DMF (7.2 mL). Stirring was continued for 3-3.5h at 65 C. Then, solvent was evaporated under reduced pressure and reaction mixture was poured into H2O (10 mL) and extracted with Et2O (3 x 10 mL). The combined organic layers were washed with brine (2 x 10 mL) and dried over Na2SO4. The solvent was removed under vacuum to afford 9, 16, 17.

According to the analysis of related databases, 2043-57-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tomaszewska, Joanna; Koroniak-Szejn, Katarzyna; Koroniak, Henryk; Arkivoc; vol. 2017; 2; (2016); p. 421 – 432;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 6940-76-7, These common heterocyclic compound, 6940-76-7, name is 1-Chloro-3-iodopropane, 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.

Intermediate 54-(3~chloropropyl)-tetrahydro-2H-pyran-4-carbonitrile. To a stirred solution of 1 M LiHMDS (25 mL, 25 mmol) in THF (10 mL) at -78 0C was added dropwise a solution of intermediate 4 (2.23 g, 20 mmol) in THF (15 mL) over 10 minutes. After 40 min, l-chloro-3-iodopropane (2.7 mL, 25 mmol) was added at once, stirred at -78 C for 1 h and 4 h room temperature. Then the reaction mixture was diluted with ether (100 mL), washed with water (20 mL) and brine (20 mL), dried (Na2SO4), filtered and concentrated to give yellow oil which was purified by flash column chromatography using 10-30% EtOAc/Hexanes to afford the product intermediate 5 as a colorless liquid (3.737 g, 99%). 1H NMR (500 MHz, CDCl3) delta: 3.97 (2H, dd, J = 11.3, 3.7 Hz), 3.71 (2H, td, J = 12.2, 1.8 Hz), 3.61 (2H, t, J = 6.3 Hz), 2.05-1.98 (2H, m), 1.88 (2H, dd, J = 13.4, 1.8 Hz), 1.77-1.74 (2H, m), 1.65-1.59 (2H, m).

The synthetic route of 6940-76-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/58646; (2007); A1;,
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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,2-Dichloro-4-iodobenzene

General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol %), 1,10-phenanthroline (20% mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

According to the analysis of related databases, 20555-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dibakar, Mullick; Prakash, Anjanappa; Selvakumar, Kumaravel; Ruckmani, Kandasamy; Sivakumar, Manickam; Tetrahedron Letters; vol. 52; 41; (2011); p. 5338 – 5341;,
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. 123158-75-8, name is 4-Chloro-2-iodo-6-nitroaniline, A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-2-iodo-6-nitroaniline

2-Amino-5-chloro-3-nitro-phenyliodide (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100 C. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%).

The synthetic route of 123158-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Life Sciences Ltd.; Kim, Sun Ha; Kim, Hyung Jin; Ku, Son Young; Jong, Chol Woong; Choe, Dok Young; Lee, Song Bae; Park, Hee Sul; Yun, Sung Hyun; Kwak, Hyo Sin; Kim, Song Wook; Saw, Dong Wook; Park, Aok; Im, Hyun Ju; Won, Jong Hon; Baek, Sung Yeop; (75 pag.)KR101511771; (2015); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 364-75-0, A common heterocyclic compound, 364-75-0, name is 1-Fluoro-4-iodo-2-nitrobenzene, molecular formula is C6H3FINO2, 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.

The synthesis was carried out following a known procedure (Serizawa et al., ?Direct Synthesis of Pentafluoroethyl Copper from Pentafluoropropionate as an Economical C2F5 Source: Application to Pentafluoroethylation of Arylboronic Acids and Aryl Bromides,? Org. Lett. 16:3456-3459 (2014), which is hereby incorporated by reference in its entirety). A 25 mL Schlenk flask (equipped with a 10 mL solid addition funnel) was flame-dried under vacuum and cooled under Ar. The flask was charged with copper(I) chloride (516 mg, 5.21 mmol; transferred in an Ar-purged glove bag) and DMF (18 mL). Sodium tert-butoxide (1.01 g, 10.4 mmol; transferred in a glove bag) was added via the addition funnel in portions over 10 mm. After replacing the addition funnel with a septum, the mixture was stirred at room temperaturefor 2.5 hours, and then was heated at 50C while ethyl 2,2,3,3,3-pentafluoropropanoate (770 jiL,5.21 mmol) was added dropwise by syringe over 2-3 mm. The reaction was stirred at 50C for 3 hours and then was cooled to 0C. Triethylamine trihydrofluoride (325 jiL, 1.99 mmol) was added dropwise over 1-2 mm by syringe, which resulted in a nearly homogeneous solution. Stirring was continued at 0C for 5 mm, and then at room temperature for 15 mm. Solid 1-fluoro-4-iodo-2-nitrobenzene (662 mg, 2.48 mmol) was added in one-portion and the reaction was heated at 80C for 12 hours, under a balloon of Ar. After the reaction had cooled to room temperature, 1 M HC1 (15 mL) was added in portions over 1-2 mm by pipet. The mixture was diluted with water (50 mL) and Et20 (50 mL), and then was filtered through a pad (3 x 3 cm) of Celite under vacuum. The filter-cake was washed with Et20 (20 mL) and the combined filtrateswere transferred to a separatory funnel. The layers were separated and the aqueous phase was extracted with Et20 (2 x 30 mL). The organic extracts were pooled, washed with a 60:40 mixture of saturated NH4C1 solution/concentrated NH4OH solution (3 x 50 mL), half saturated NaC1 solution (2 x 50 mL) and brine (50 mL), dried (Mg504), and filtered. Concentration under vacuum gave 670 mg of an orange oil, which was used without further purification (seesynthesis of APS5-1 1).

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; ICHAN SCHOOL OF MEDICINE AT MOUNT SINAL; DAR, Arvin, C.; CAGAN, Ross, L.; SCOPTON, Alex, P.; SONOSHITA, Masahiro; (175 pag.)WO2018/35346; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5458-84-4, name is 1-Iodo-2-methoxy-4-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 5458-84-4, Quality Control of 1-Iodo-2-methoxy-4-nitrobenzene

A mixture of Cu l (6.80 g, 35.84 mmol ), CsF ( 14. 15 g, 93.18 mmol ) l -iodo-2-methoxy- 4-nitrobenzene ( 10 g, 35.84 mmol ) and sulfolane (20 ml ), was stirred rapidly at 45 C. To this mixture was added trimethyl(trifluoromethyl)silane ( 13.25 g, 93. 1 mmol ) dropwise over 4 hours using a syringe pump, and the resulting mixture was stirred at 45C for 1 8 hours. The mixture was diluted with ethyl acetate (500 mL ) and stirred with Celite for 5 min. The reaction mixture was filtered through a pad of Celite, diluted with ethyl acetate ( 500 mL ). The organic layer was washed with 10% NH4OH, 1.0 N HCl, brine, dried over Na2SC>4, filtered, and concentrated to give the crude product.The crude product was purified by chromatography (ethyl acetate/petroleum ether 0/1 to 1/4) to give intermediate 444 (8 g, 91% yield ) as a white solid.

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, 1-Iodo-2-methoxy-4-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 74534-15-9, name is 1-Chloro-2-iodo-4-nitrobenzene, 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. name: 1-Chloro-2-iodo-4-nitrobenzene

A dried round flask charged with 1-chloro-2-iodo-4-nitrobenzene (17.0 g, 60 mmol), 3,5-dimethylisoxazol-4-ylboronic acid (25.4 g, 180 mmol), Pd(Ph3P)4 (3.47 g, 3.0 mmol) and Ba(OH)28H20 (37.9 g, 120 mmol) in DME (315 mL) and water (93 mL) was evacuated and refilled with N2 gas in several times. The reaction mixture was stirred at 80 C for 16 hours, cooled to room temperature and quenched with water. The mixture wasextracted with EtOAc twice. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on Si02 (Hex/EtOAc = 9:1) to afford the titled compound (5.5 g, 36%) as a yellow solid.?H-NMR (400 MHz, CDC13): oe 8.20 (dd, J 8.4, 2.0 Hz, 1H), 8.09 (d, J= 2.0 Hz, 1H), 7.68 (d, J= 8.4 Hz, 1H), 2.31 (s, 3H), 2.16 (s, 3H).

The synthetic route of 1-Chloro-2-iodo-4-nitrobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAINOS MEDICINE, INC.; CHOI, Minjeong; OH, Su-Sung; (113 pag.)WO2016/186453; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com