Author: Jessica.F

Some common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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. Computed Properties of C7H8FNO

Compound a1-2 (8.0 g, 43 mmol) was placed in a 500 mL single-necked reaction flask and concentrated sulfuricacid (100 mL) was added under stirring at a constant rate to dissolve the substrate. Concentrated nitric acid (6.15 mL,48 mmol) was slowly added dropwise to the stirred reaction flask at -20 C and stirred at that temperature for 5 minutes.The progress of the reaction was checked by TLC. After the reaction of the substrate was complete, the reaction mixturewas poured into iced water. In -20 C ice bath, the aqueous solution of hydroxide/water (150 mL/300 mL) was slowly added to the reaction system and pH was adjusted to 8-9. After neutralization, the reaction solution was extracted threetimes with ethyl acetate/water system. The organic layer was separated, washed with water and then saturated brine,dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the compound 4-fluoro-2-methoxy-5-nitroaniline a1 (8.7 g) which was directly used in the next step. Yield: 80%; purity: 100%; MS m/z(ESI): 187.0 [M+H]+;1HNMR (400 MHz, DMSO-d6): delta 7.34 (d, J = 7.8 Hz, 1H), 7.04 (d, J = 13.4 Hz, 1H), 5.25 (brs, 2H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 450-91-9, its application will become more common.

Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co., Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; LEI, Jing; WEN, Chong; ZHANG, Zhiyuan; HE, Xiangyu; (57 pag.)EP3173412; (2017); A1;,
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Related Products of 24332-20-5, 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. 24332-20-5 name is 1,1,2-Trimethoxyethane, 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.

To a solution of methoxyacetaldehyde dimethylacetal (5 g, 41.63 mmol) in methanol (20 ml) was added a solution of hydroxylamine hydrochloride (2.9 g, 41.73 mmol) in water (10 ml). The reaction was stirred at room temperature for 18 hours. To the reaction was then added an aqueous solution of sodium hydroxide (1.67 g, 41.6 mmol in 10 ml water) and stirred for 3 hours at room temperature. The methanol was removed in vacuo and the mixture acidified with concentrated hydrochloric acid to pH 5-6, before extracting with f-butylmethyl ether, drying over Na2SO4 and concentrating in vacuo to afford the title compound as a 1.5:1 mixture of E/Z isomers (2.64 g, 71% yield).1HNMR (CDCI3): 3.4 (m, 3H), 4.05 (d, 1.2H), 4.3 (d, 0.8H), 6.9 (t, 0.4H), 7.5 (t, 0.6H), 8.55 (br s, 0.6H), 8.85 (br s, 0.4H)

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

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
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Electric Literature of 16452-01-0, 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. 16452-01-0, name is 3-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 6-Methyl-7-methoxy-quinolineglycerol(2.5 eq) FeSO4«7H2O( 0.03 eq)[0182] Using a minimal amount of dioxane, 3-methoxy-4-methylaniline (5.00 g, 36.5 mmol) was slowly added to a mixture of sodium m-nitrobenzenesulfonate (6.62 g, 29.4 mmol), MsOH (20 mL), and FeSO4*7H2O (0.39 g, 1.4 mmol) in a 10OmL round bottom flask heated to an internal temperature of 145-155 0C. Glycerol( 10.75 g, 116.8 mmol) was then added dropwise via addition funnel while keeping the internal temperature at 145-155C. After addition, the reaction was stirred in a 150 0C oil bath until LCMS indicated completion (4-6 h). After being cooled to rt, ice (2Og) was added, then the solution was neutralized with IO N NaOH (calculated to same eq of MsOH) at a speed to keep the internal temperature below 40 0C. A thick suspension appeared after addition, and this was extracted with EtOAc (50 mL x 3). The organic layer was filtered through a Celite pad to remove insoluble black particles and then purified by flash column chromatography on silica gel to give the desired product (5.0 g, 79%). MS (ES) mlz 174.1 (M+ H+).

The chemical industry reduces the impact on the environment during synthesis 3-Methoxy-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Pinchen; GLEASON, Mark, M.; JAEN, Juan, C.; LI, Lianfa; MCMAHON, Jeffrey, P.; POWERS, Jay; ZENG, Yibin; ZHANG, Penglie; WO2010/54006; (2010); A1;,
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Synthetic Route of 36942-56-0, 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. 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2.5M nBuLi (1.8 mL, 4.5 mmol) was added dropwise over 5 minutes into a mixture of 2-bromo-4-methoxy-1-methylbenzene (750 mg, 3.73 mmol) in anhydrous THF (30 mL) at -78 C. After the mixture was stirred at -78 C. for 20 minutes, anhydrous trimethyl borate (0.62 g, 6 mmol) was added into the solution at -78 C. The reaction mixture was brought to room temperature for over period of 2 h. The reaction was quenched by 2N HCl (1 mL). The THF was removed by vacuum. The crude product was diluted with 2N HCl (100 mL). The acidic solution was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate fraction was dried over sodium sulfate. The sodium sulfate was removed by filtration and the solvent was removed by vacuum to yield a pale yellow solid (0.43 g, 69%).

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-Bromo-4-methoxy-1-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); A1;,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-4-fluoro-2-methoxybenzene

A solution of dry diisopropylamine (10 g, 99 mmol) in dry THFunder nitrogen was cooled with a -78 C bath, n-butyl lithium (2.50 M in hexane, 40 mL, 99 mmol) was added andthe solution was stirred at -78 C for 20 minutes. 1-Bromo-4-fluoro-2-methoxybenzene (17.0 g, 82.5 mmol) wasadded. After stirring at -78 C for 2 hours, the solution was bubbled with CO2 and then warmed to 0 C. Then 1 NHCl was added until pH=3-4 and the mixtue was extracted with AcOEt. The combined organic layers were washedwith brine, dried over anhydrous sodium sulphate and concentrated to afford 3-bromo-6-fluoro-2-methoxybenzoicacid.

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
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Application of 1663-61-2, 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. 1663-61-2, name is (Triethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Method B (microwave irradiation) – The reaction mixture composed of cinnamic acid hydrazide 2 (0.50 g, 3.0 mmol), triethyl orthoester (6.0 mmol) and 2 mL of glacial AcOH was placed into 10 mL crimp-sealed thick-walled glass tube. The reaction vessel was placed in CEM Discover microwave-enhanced synthesis system operating at 125 +/- 5 C, power 250 W and kept for 10 min. After cooling, the excessive orthoester and AcOH were evaporated under reduced pressure. The crude product was purified by column chromatography with silica gel and an eluent of benzene/AcOEt, 1:5, v/v.

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, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Tetrahedron Letters; vol. 53; 1; (2012); p. 76 – 77;,
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Synthetic Route of 105404-89-5, 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. 105404-89-5, name is 2,7-Dibromo-3,6-dimethoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,7-dibromonaphthalene (300 mg, 1.05 mmol) in1,4-dioxane (10 mL) were added 4-nitrophenylboronic acid (381 mg, 2.28 mmol), Pd(PPh3)4 (28 mg, 0.024 mmol), and aq. Cs2CO3 (2 M, 2 mL), and the reaction mixture was stirred overnight at reflux under Ar. Then, the reaction mixture was diluted with water (30 mL), and the product was extracted with chloroform (100 mL × 3). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography [hexane/chloroform (2:1)] to give 2,7-bis(4-nitrophenyl)naphthalene 3a (326 mg, 0.879 mmol, 84%) as a yellow 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, 2,7-Dibromo-3,6-dimethoxynaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hachiya, Sojiro; Asai, Kengo; Konishi, Gen-Ichi; Tetrahedron Letters; vol. 54; 14; (2013); p. 1839 – 1841;,
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Reference of 768-70-7, A common heterocyclic compound, 768-70-7, name is 3-Ethynylanisole, molecular formula is C9H8O, 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: General produce: o-iodophenol (0.5 mmol), alkyne (1.0 mmol) andbase (1.0 mmol) were added into a 10 mL dry Schlenk tube under Ar,then anhydrous DMF (5 mL) was injected into the mixture using syringe.Then the solution stirred at preheated oil bath (160 C). The reactionwas monitored by TLC and GC.The mixture was cooled down toroom temperature after full conversion, then diluted with dichloromethaneand washed with water three times. The organic layerwas separated and washed with brine followed by drying with anhydrousNa2SO4. The filtrate was concentrated in vacuo to afford thecrude product, which was purified by flash column chromatography onsilica gel (petroleum ether).

The synthetic route of 768-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ji, Guijie; Duan, Yanan; Zhang, Shaochun; Yang, Yong; Catalysis Today; (2019); p. 101 – 108;,
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Synthetic Route of 61367-43-9, 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. 61367-43-9, name is cis-4-Methoxycyclohexanamine hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 284 6-(4-(4-cyano-2-fluorophenyl)-5-hydroxy-lH-pyrazol-l-yl)-N- ((ls,4s)-4-methoxycyclohexyl)nicotinamide [01159] [01160] Combined EDC (1 15 mg, 0.601 mmol), HOBT (27.1 mg, 0.200 mmol), (cis)-4- methoxycyclohexanamine hydrochloride (66.4 mg, 0.401 mmol) and 6-(4-(4-cyano-2- fluorophenyl)-5 -hydroxy- lH-pyrazol-l-yl)nicotinic acid (65 mg, 0.200 mmol) in DMF (0.8 mL) and then added DIPEA (0.175 mL, 1.002 mmol). After 24 hours, the reaction mixture was purified by preparative HPLC (ACN/water with formic acid) to give the title compound (23 mg, 0.053 mmol, 26.3 %) as a tan solid. MS: 436 (M+H). NMR (400 MHz, DMSO- de) 5 ppm 1.34 – 1.48 (m, 2 H) 1.49 – 1.65 (m, 4 H) 1.76 – 1.88 (m, 2 H) 3.17 (s, 3 H) 3.31 (br. s., 1 H) 3.73 – 3.87 (m, 1 H) 7.62 (dd, J=8.2, 1.6 Hz, 1 H) 7.77 (dd, J=1 1.7, 1.6 Hz, 1 H) 8.16 (d, J=3.0 Hz, 1 H) 8.31 – 8.44 (m, 3 H) 8.55 (t, J=8.0 Hz, 1 H) 8.84 (dd, J=2.0, 1.0 Hz, 1 H) 13.71 (br. s., 1 H).

The synthetic route of cis-4-Methoxycyclohexanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
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Reference of 51344-14-0, A common heterocyclic compound, 51344-14-0, name is N,N-Dimethyl-2-(p-tolyloxy)ethanamine, molecular formula is C11H17NO, 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 test tube containing a magnetic bar was added aryl halide (1.0 mmol), Cu2O (14.3 mg, 0.1 mmol), KOH (169 mg, 3.0 mmol), 2-dimethylaminoethanol (0.3 mL, 3.0 mmol), and DMSO/H2O (1.5 mL/0.5 mL). After flushing with argon, the mixture was stirred in a preheated oil bath at 100 C for 24 h. After cooled to ambient temperature, the reaction mixture was distributed in aqueous HCl (5 %) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under vacuum. The crude product was further purified by column chromatography (EtOAc/n-Hexane) to provide the phenols.

The synthetic route of 51344-14-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Jihye; Battsengel, Oyunsaikhan; Liu, Yajun; Chae, Junghyun; Bulletin of the Korean Chemical Society; vol. 36; 12; (2015); p. 2833 – 2840;,
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