Author: Jessica.F

Synthetic Route of 22236-10-8, A common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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.

To a suspension of p-toluenesulfonic acid monohydrate (9.25 g, 48.6 mmol) in acetonitrile (65 mL)4- (difluoromethyloxy) aniline (2.00 mL, 16.2 mmol) was added at room temperature.To the reaction solution was added dropwise a solution of sodium nitrite (2.24 g, 32.4 mmol) and potassium iodide (6.72 g, 40.5 mmol) in water (11 mL) at 10 C., and the mixture was stirred at room temperature for 3 hours did.Water was added to the reaction solution,And extracted with ethyl acetate.The combined organic layers were successively washed with a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained crude product was purified by column chromatography (hexane) to obtain a pale pink oil (3.98 g, yield: 91%) of 1-difluoromethyloxy-4-iodobenzene.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; HOKKO CHEMICAL INDUSTRY COMPANY LIMITED; HANDA, MASAMI; MIZUTA, SATOSHI; HIRAI, KENJI; OKAMURA, DAIGO; GUSHIKAWA, TORU; (111 pag.)JP2015/848; (2015); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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: A flask is charged with bromoaryl derivative (1 eq.), piperazine (4-6 eq.), BINAP (0.06-0.22 eq.), NaOtBu (1.4-2.5 eq.) and toluene. The reaction mixture is degassed with N2 and Pd2(dba)3 (0.03-0.11 eq.) is added. Reaction mixture is heated at 100-110C for 2h-20h. The reaction mixture is extracted with HCl 1N solution. The aqueous layer is basified with NaOH 2N solution and extracted with EtOAc or DCM. The combined organic layers are washed with water and brine, dried (over anhydrous Na2SO4 or MgSO4), filtered and concentrated in vacuo to afford the expected arylpiperazine used without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; DE CEUNINCK, Frederic, Andre; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (180 pag.)WO2017/211666; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 25245-34-5, 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. 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2,5-Dimethoxyphenylboronic acid (Structure 37 of Scheme XI, where R1 =H, R2 =methoxy) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 1-bromo-2,5-dimethoxybenzene (2.00 mL, 13.3 mmol), n-BuLi (2.5M in hexanes; 5.34 mL, 13.3 mmol), and trimethylborate (4.5 mL, 40 mmol) to afford 2.43 g (99%) of 2,5-dimethoxyphenylboronic acid which was used without further purification.

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

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The synthetic route of 3,5-Dimethoxyphenylacetylene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 19056-40-7, name is 4-Bromo-3-methoxyaniline, belongs to ethers-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 19056-40-7, HPLC of Formula: C7H8BrNO

To a solution of 4-bromo-3-methoxyaniline (2.0 g, 9.9 mmol) in CH2Cl2 (25 mL) at 0 C. was added Et3N (4.1 mL, 29.7 mmol), followed by dropwise addition of Ac2O (1.4 mL, 14.9 mmol). The reaction mixture was stirred under argon at 0 C. for 0.5 hour and at room temperature overnight, diluted with CH2Cl2 (25 mL) and water (25 mL). The organic layer was further washed with 1 N acetic acid aqueous solution (25 mL), saturated NaHCO3 aqueous solution (25 mL), brine (25 mL), dried (MgSO4). Evaporation to dryness yielded the title product (2.2 g) as a tan solid. 1H NMR (300 MHz, DMSO-d6) delta 2.04 (s, 3H), 3.80 (s, 3H), 7.10 (dd, J=2.0 Hz and 8.6 Hz, 1H), 7.44 (m, 2H), 10.1 (s, 1H).

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-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ruan, Fuqiang; (35 pag.)US2019/308963; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, belongs to ethers-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 7252-83-7, HPLC of Formula: C4H9BrO2

Acid 101 (all material prepared in the previous step, 10.9 mmol) was dissolved in 150 mL of DMF. Powdered K2CO3 (25 g, 180 mmol) was added to the solution followed by adding of bromoacetaldehyde dimethyl acetal (33.3. mL, 283 mmol). The reaction mixture was stirred overnight at 110 C. DMF solution was removed from the flask (leaving insoluble material in the flask) and evaporated. The residue was mixed with 150 mL of water and combined with the solid left in the flask. The product was extracted with ethyl acetate (4¡Á45 mL), combined extracts were washed with water (4¡Á30 mL), brine (30 mL), dried over sodium sulfate and evaporated in vacuum. The residue was dissolved in chloroform, loaded on silica gel column (packed in 100:3 chloroform-EtOAc mixture). The column was eluted with 100:3 chloroform-EtOAc mixture. Pure fractions containing the product were combined and evaporated to give ester 102 as a clear oil, solidified later to form white solid (4.54 g, 66%).

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

Reference:
Patent; Life Technologies Corporation; CORRY, Schuyler; Downey, William; Filanoski, Brian; Gee, Kyle; Greenfield, Lawrence; Hirsch, James; Johnson, Iain; Rukavishnikov, Aleksey; (129 pag.)US2016/139135; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 29578-39-0, These common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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.

Step 2 3-Bromo-5-fluorophenol To a solution of 1-bromo-3-fluoro-5-methoxybenzene (3.0 g, 0.015 mol) in dry CH2Cl2 (80 mL) under an inert atmosphere and cooled to -30 C. was added 1 M BBr3 (4.27 mL, 0.045 mol) in 21 mL of CH2Cl2 dropwise while maintaining temperature at -30 C. The reaction was stirred for 3 h at 0-5 C. and then the reaction mixture was quenched with aqueous saturated NaHCO3. Water was added and the mixture was extracted with CH2CO2 three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (2.54 g, 91%).

The synthetic route of 29578-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FAY, Lorraine Kathleen; Johnson, Douglas S.; Kesten, Suzanne Ross; Lazerwith, Scott E.; Morris, Mark Anthony; Stiff, Cory Michael; Meyers, Marvin Jay; Wang, Lijuan Jane; US2008/261941; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, belongs to ethers-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 111-95-5, SDS of cas: 111-95-5

Example 2 8.0 g (60 mmol) of bis(methoxyethyl) amine was added to 100 ml of dehydrated dichlorrmethane in a flask followed by Ar gas replacement. Thereafter, 8.8 g (87 mmol) of triethyl amine was added thereto. Next, the system was cooled down to about -10 C. 6.5 g (72 mmol) of acrylic acid chloride was slowly dropped in the system while keeping the temperature in the system ranged from -10 C. to -5 C. and thereafter stirred for two hours at room temperature. Furthermore, subsequent to removal of precipitants by filtration, the filtrate was washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution. Next, subsequent to drying by sodium sulfate, the dried resultant was condensed under a reduced pressure to obtain an oily brown material. (0184) Furthermore, by a column chromatography filled with 300 g of Wakogel C300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexane and ethyl acetate as eluate, the oily brown material was fined to obtain 5.5 g (yield: about 50%) of an oily, pale yellow material represented by the following chemical formula. 1H-NMR (CDCl3): delta3.34 (d, 6H), 3.51 (t, 2H), 3.57 (t, 2H), 3.63 (t, 4H), 5.67 (dd, 1H), 6.34 (dd, 1H), 6.64-6.69 (m, 1H) IR(NaCl): 2982, 2930, 2981, 2829, 1651, 1613, 1447, 1366, 1315, 1270, 1230, 1193, 1157, 1118, 1069, 1015, 981, 962, 824, 795, 529 cm-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Bis(2-methoxyethyl)amine, and friends who are interested can also refer to it.

Reference:
Patent; Ricoh Company, Ltd.; Morita, Mitsunobu; Noguchi, Soh; Kimura, Okitoshi; (28 pag.)US9593248; (2017); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, A new synthetic method of this compound is introduced below., SDS of cas: 702-24-9

General procedure: A solution of 2-methyl-4-chlorocyclopenta[d]pyrimidine (17, 1eq.) and appropriate anilines or benzylamines (1.05 eq.) wereplaced in dioxane in a microwave vial. To the solution, HCl (2Nin dioxane, 1?2 drops) was added. The reaction mixture was setin a Biotage microwave initiator at 120 C for 3?6 h with pressure<4 bar. The reaction was cooled and transferred to a flask, and thesolvent was evaporated at reduced pressure. The residue wasdiluted with EtOAc, neutralized with NH4OH, and then washedwith water (2 10 mL). After drying with anhydrous Na2SO4, theorganic solvent was concentrated in a rotary evaporator to <1mL. This residue was placed on top of a silica gel column and elutedwith hexane and EtOAc or with CHCl3 and MeOH. Fractions containingthe product (TLC) were pooled and evaporated to affordpure compounds 3?7, 9?14. 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; Xiang, Weiguo; Choudhary, Shruti; Hamel, Ernest; Mooberry, Susan L.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2437 – 2451;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 24332-20-5, name is 1,1,2-Trimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1,2-Trimethoxyethane

A solution of 1,1,2-trimethoxyethane (838 mg, 6.9 mmol, 901.3 uL) in water (22.0 mL) and HC1 (0.3 mL, 2M) was stirred at 60C for 2h, then extracted with dichloromethane (10.0 mL x 3). The combined organic layers were washed with brine (30.0 mL x 3), dried over Na2 SO4, filtered to give a filtrate. To the filtrate was added the solution of 2-((lr,4r)-4- aminocyclohexyl)isoindoline-1,3-dione (500 mg, 1.4 mmol, TFA) with TEA to pH 7 in MeOH (30.0 mL) and CH3COOH (125 mg, 2.0 mmol, 119.7 uL). And then NaBH3CN (175 mg, 2.7 mmol) was added to above reaction mixture and CH3COOH was added to adjusted pH to 5. The mixture was stirred at 60C for 12 h. The reaction mixture was extracted with dichloromethane (30.0 mL x 3). The combined organic layers were washed with brine (30 mL x 3), dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-((lr,4r)-4-((2- methoxyethyl)amino)cyclohexyl)i soindoline- 1,3 -dione (410 mg, crude).

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 24332-20-5.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (143 pag.)WO2018/222917; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem