Author: Jessica.F

Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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. SDS of cas: 3401-47-6

Under argon, in a flame-dried vessel, a solution of 1-bromo-2-methoxynaphthalene (7.67 g, 32.36) in THF (50 ml) was added dropwise to the magnesium (0.905 g, 37.2 mmol) in THF (15 ml). The reaction mixture was stirred at room temperature for 2 h then at 50C for 1h. It was then cooled to -78C and trimethylborate (11.4 ml, 101.7 mmol) was slowly added. After 2 h at -78C, the mixture was allowed to warm to room temperature and stirred overnight. After addition of water (40 ml), THF was removed under reduced pressure. The mixture was extracted with dichloromethane; the combined organic phases were dried over MgSO4, filtered and concentrated. Recrystallization from dichloromethane gave the boronic acid as a white powder (80% yield). 1H NMR (400.14 MHz, CDCl3): d = 4.08 (s, 3H), 6.22 (s, 2 H), 7.28 (d, J = 9.1 Hz, 1H), 7.34-7.43 (m, 1H), 7.47-7.56 (m, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.98 (d, J = 8.9 Hz, 1H), 8.86 ppm (d, J = 9.1 Hz, 1H); 13C{1H} NMR (75.47 MHz, [D6]DMSO): d = 56.1, 113.7, 121.8, 122.7, 125.8, 127.4, 127.8, 128.5, 129.4, 135.6, 159.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3401-47-6, its application will become more common.

Reference:
Article; Castillo, Angelica Balanta; Perandones, Bernabe F.; Zangrando, Ennio; Gladiali, Serafino; Godard, Cyril; Claver, Carmen; Journal of Organometallic Chemistry; vol. 743; (2013); p. 31 – 36;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: At 0 C, a solution of 3(4)-bromobenzoyl chloride or 5-bromothiophene-2-carbonyl chloride (1 eq) in CH2Cl2 (2 ml/eq) was added drop wise to a solution of N-methylbenzylamine (1 eq) and triethylamine (1.15 eq) in CH2Cl2 (2 ml/eq). The mixture was kept stirred at 0 C for 3 h and evaporated under reduced pressure. The residue was purified by FC with n-hexane/ethyl acetate as eluant.

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Kuiying; Al-Soud, Yaseen A.; Wetzel, Marie; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5978 – 5990;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 74137-36-3, These common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-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.

To a solution of 20b (60 g, 0.2256 mol) and anhydrous Et2O (1 L)cooled to -78¡ã C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78¡ã C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78¡ã C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30¡ã C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10¡ã C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5percent EtOAc) to afford 21.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2007/88015; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 41789-95-1, The chemical industry reduces the impact on the environment during synthesis 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

General procedure: An amine (1 mmol, 2 equiv) was added to a solution of Nchlorosuccinimide(149 mg, 1.1 mmol, 2.2 equiv) in CH2Cl2(5 mL) at r.t. in the dark. After 3 h, Ir(dtbpy)(ppy)2PF6 (4 mg,5 mumol, 0.01 equiv), Ph3N (245 mg, 1 mmol, 2 equiv), andbenzoxazole (60 mg, 0.5 mmol, 1 equiv) were added. Thereaction rube was sealed and placed at a distance of 5 cm from 3 W blue LED and stirred for 60 h. After the reactionwas complete, the solvent was evaporated under vacuo. Thecrude mixture was purified by flash column chromatographyeluting with a mixture of PE-EtOAc

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Jia-Di; Liu, Yu-Xia; Xue, Dong; Wang, Chao; Xiao, Jianliang; Synlett; vol. 25; 14; (2014); p. 2013 – 2018;,
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. 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,4-Dibromo-2,5-dimethoxybenzene

The 1,4-dibromo-2,5-dimethoxybenzene (T-13) (25.0g, 84.47mmol, Tokyo Kasei Kogyo),4-methoxyphenyl boronic acid (T-14) (28.2g, 185.84mmol, Tokyo Kasei Kogyo),Bis (di – t-butyl (4-dimethylaminophenyl) phosphine) dichloropalladium (II)(0.30g, 0.42mmol),Trisodium phosphate dodecahydrate (96.33g, 253.42mmol),Tetrabutylammonium bromide (TBAB) (5.45g, 16.89mmol),Toluene (100ml), isopropanol (100ml)And water(100ml) were mixedIt was heated at reflux for 5 hours.The reaction mixture was allowed to cool to room temperature filtered,The filtrate was washed with water (200ml) and saturated brine (100ml) washedDried over anhydrous magnesium sulfate,Concentrated under reduced pressure.By column chromatography (the eluent:Toluene / ethyl acetate = 9/1 (volume ratio)) and the residue was purified,To obtain the compound (T-15) (27.9g, 84.47mmol, 94.3%).

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; JNC Co., Ltd.; JNC Petrochemical Co., Ltd.; Kobayashi, Masahide; Goto, Yasuyuki; Kobayashi, Takahiro; (94 pag.)CN105358523; (2016); A;,
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. 106854-77-7, name is 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

1-BROMO-4- (2, 2,2-trifluoroethoxy) benzene (1) (0.85 g, MW 255.03, 1.5 eq), pinacol diborane (from Aldrich, 0.89 g, MW 253.95, 1.6 eq), potassium acetate (from Aldrich, 0.86 g, MW 98.15, 4.0 eq), and (1, 1′-BIS (diphenylphosphino)- ferrocene) dichloropalladium (II) complex with dichloromethane (from Aldrich, 54 mg, MW 816.64, 0.03 eq) were charged in a round-bottom flask. The flask was purged with N2. N, N-DIMETHYLFORMAMIDE (from Aldrich, 8.0 ml) was then added, and the mixture was stirred at 80C for 2 hr. Tert-butyl 4-[(6-BROMOPYRIDIN-3-YL) SULFONYL] tetrahydro-2H-pyran- 4-carboxylate (2) (0.90 g, MW 406.29) was then added, along with sodium carbonate solution (2 M aqueous, 5.5 ml, 5 eq) and additional palladium complex (above, 54 mg, 0.03 eq). The reaction was continued at 80C for 3 hr. Afterward, the mixture was cooled to room temperature and filtered through a Celite pad. The filter cake was washed with ethyl acetate (2 x 50 ml). The filtrate and washes were then combined and washed with water (3 x 100 ml) and brine (1 x 100ML). The organics were then dried over sodium sulfate and concentrated to form a black residue. The residue was chromatographed (silica gel, ethyl acetate: hexanes, 1: 5) to afford TERT-BUTYL-4- (F 6- [4- (2, 2,2- TRIFLUOROETHOXY) phenyl] pyridin-3-yl} sulfonyl) tetrahydro-2H-pyran-4-carboxylate (3) as a white solid (0.26 g, 24 % yield). The product (3) was confirmed by LCMS. The “equivalents”above indicate equivalents relative to the charged amount OF TERT-BUTYL 4- [ (6- bromopyridin-3-yl) sulfonyl] TETRAHYDRO-2H-PYRAN-4-CARBOXYLATE.

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; PHARMACIA CORPORATION; WO2004/48368; (2004); A2;,
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. 456-49-5, name is 1-Fluoro-3-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Fluoro-3-methoxybenzene

The 3-fluoro anisole (15 g, 119 mmol) was placed in THF (300 mL) and cooled to about -78 C., and then n-BuLi (89 mL 1.6 M in hexanes) was added while maintaining the temperature at around -70 C. The mixture was stirred for about 15 minutes, and bromine (18.9 g, 119 mmol) was added over 10 minutes. The mixture was warmed to r.t. and stirred overnight. The mixture was quenched with water, diluted with ether (500 mL) and partitioned between water/ether (1/1 300 mL). The water layer was back extracted with ether (250 mL), and the combined organic fractions were dried, filtered and concentrated. The dark residue was distilled under house vacuum (product 115-130 C.) to recover about 13.8 g of the product as a gray oil (57%/).

According to the analysis of related databases, 456-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Briner, Karin; Doecke, Christopher William; Mancuso, Vincent; Martinelli, Michael John; Richardson, Timothy Ivo; Rothhaar, Roger Ryan; Shi, Qing; Xie, Chaoyu; US2004/82590; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 10385-36-1, The chemical industry reduces the impact on the environment during synthesis 10385-36-1, name is 1-Bromo-2,3,4-trimethoxybenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 10 1-(2,3,4-Trimethoxyphenyl)-2,2,4,4-tetramethyl-3-(4-phenylpiperazinyl)-cyclobutanol-(1) Prepared from 2,2,4,4-tetramethyl-3-(4-phenyl-piperazinyl)-cyclobutanone by Grignard reaction with 2,3,4-trimethoxy-bromobenzene in tetrahydrofuran. Yield: 14% of theory; m.p. of the cis-compound: 148-150C (from ethyl acetate).

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-Bromo-2,3,4-trimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim GmbH; US3931185; (1976); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of the azide intermediate (0.1 mmol) in 0.2 mL of DMFin a microwave tube, CuSO4 (0.05 mmol) diluted in 50.0 muL of water,sodium ascorbate (0.025 mmol) and the alkyne (0.2 mmol) were added.The tube was sealed and the solution was irradiated (70 C, 150 W) for10 min and, then, TLC analysis showed the complete consumption ofthe starting material. The reaction was diluted with 15 mL of brine,extracted with ethyl acetate (3¡Á10 mL), dried by anhydrous Na2SO4and concentrated under reduced pressure. The resulting crude productwas purified by column chromatography on silica gel [hexane: ethylacetate, 60:40% (v/v)] yielding the expected product.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dimethoxyphenylacetylene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zimmermann, Lara A.; de Moraes, Milene H.; da Rosa, Rafael; de Melo, Eduardo B.; Paula, Favero R.; Schenkel, Eloir P.; Steindel, Mario; Bernardes, Lilian S.C.; Bioorganic and Medicinal Chemistry; vol. 26; 17; (2018); p. 4850 – 4862;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 6487-99-6, These common heterocyclic compound, 6487-99-6, name is 2-(3-Methylphenoxy)ethylamine, 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.

A solution of Example IB (25 mg, 0.08 mmol) in N,N-dimethylformamide (1.0 mL) was treated with a solution of 2-(3H-[l ,2,3]triazolo[4,5-]pyridin-3-yl)- l, 1 ,3,3- tetramethylisouronium hexafluorophosphate(V) (35 mg, 0.09 mmol) in N,N-dimethylformamide (0.5 mL). Then a solution of 2-(m-tolyloxy)ethanamine (12 mg, 0.08 mmol) in N,N- dimethylacetamide (0.15 mL) was added followed by N,N-diisopropylethylamine (0.037 mL, 0.21 mmol). The reaction was shaken at ambient temperature overnight and purified by HPLC (2-coupled C8 5 mupiiota 100 A columns 30 mm x 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid in water)) to provide the title compound. JH NMR (400 MHz, DMSO-Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem