Month: June 2021

Related Products of 944317-92-4, 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. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

The synthetic route of 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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These common heterocyclic compound, 80936-82-9, name is 4-(Methoxymethyl)aniline, 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. Safety of 4-(Methoxymethyl)aniline

Step 2: Synthesis of 7-(tert-butyl)-N-(4-(methoxymethyl)phenyl)-4-(methylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide 7-(tert-butyl)-5-iodo-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine obtained in step 1, 103 mg of 4-(methoxymethyl)aniline, 90 mul of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 24 mg of 1,1′-bis(diphenylphosphino) ferrocene-palladium (II) dichloride-dichloromethane complex were added to 1 mL of DMA, and the mixture was stirred in a carbon monoxide atmosphere at 110 C. for 2 hours. The obtained reaction solution was purified by silica gel chromatography (developing solvent: hexane-ethyl acetate), concentrated, and purified again by basic silica gel chromatography, followed by concentration, thereby obtaining 52 mg of the title compound.

The synthetic route of 4-(Methoxymethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); A1;,
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Electric Literature of 707-07-3, 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. 707-07-3 name is (Trimethoxymethyl)benzene, 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 stirred solution of 14 (1.40 g, 3.74mmol) inCH2Cl2 (5 mL)was added trimethylorthobenzoate (1.44 mL, 7.48 mmol). The mixture was treated with a catalyticamount of (+)-10-camphorsulfonic acid at 25C for 30 min, and then the solutionwas concentrated. To the residue was added 80% HOAc, and after stirring 10 min,themixture was concentrated. The residue was purified by flash column chromatography(petroleum ether/ethyl acetate, 3:1) to yield 5 (1.45 g, 81%) as a syrup. 1HNMR (600 MHz, CDCl3): delta 8.12-8.07 (m, 4H, ArH), 7.63-7.57 (m, 2H, ArH), 7.48(t, J=7.2Hz, 1H, ArH), 7.47 (t, J=7.2Hz, 1H, ArH), 7.40 (d, J=7.8Hz, 2H, ArH),7.13 (d, J=7.8Hz, 2H, ArH), 5.64 (dd, J=3.6, 1.8Hz, 1H,H-2), 5.58 (d, J=1.2Hz,1H, H-1), 5.32 (t, J = 9.6 Hz, 1H, H-4), 4.57 (m, 1H, H-5), 4.33-4.27 (m, 1H, H-3),2.52 (d, J = 7.8 Hz, 1H, -OH), 2.32 (s, 3H, -SPhCH3), 1.34 (d, J = 6.0 Hz, 3H, H-6); 13C NMR (150 MHz, CDCl3): delta 167.15, 165.87, 138.16, 133.58, 133.56, 132.40,129.95, 129.88, 129.87, 129.84, 129.61, 129.30, 129.28, 128.57, 128.54, 128.06, 86.21,75.74, 74.78, 69.70, 67.42, 21.12, 17.53; ESI HRMS: calcd for (C27H26O6S+Na+)m/z, 501.1342; found, 501.1354.

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

Reference:
Article; Zhang, Xin; Wang, Dongyue; Jin, Guoxia; Wang, Lizhen; Guo, Zhongwu; Gu, Guofeng; Journal of Carbohydrate Chemistry; vol. 36; 4-6; (2017); p. 189 – 204;,
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Synthetic Route of 6738-23-4,Some common heterocyclic compound, 6738-23-4, name is 2,4-Dimethylanisole, molecular formula is C9H12O, 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 A Preparation of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide To a solution of 2.72 g. (0.02 mole) of 2,4-dimethylanisole in 20 ml. of acetic acid and 2 ml. of sulfuric acid was added (2.47 g., 0.02 mole) 2-chloro-N-(hydroxymethyl)acetamide at < 20 C. over a 10 minute period with stirring. After standing at room temperature about 20 hours the mixture was poured with stirring into 250 ml. of ice-water. After 1 hour the precipitate was collected, washed with water and dried at 60 C. and recrystallized 3 times from methanol:water (3:2), once from ethanol:water (3:2) and twice from ethanol:water (1:1) to give 0.34 g. of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide, m.p. 124-124.5 C. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dimethylanisole, its application will become more common. Reference:
Patent; Merck & Co., Inc.; US4092414; (1978); A;,
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Application of 41365-75-7, 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. 41365-75-7 name is 1-Amino-3,3-diethoxypropane, 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.

Intermediate 6; EPO To a solution of Intermediate 4 (1.40 g, 3.49 mmol), 1 -amino-2,3-diethoxypropane (513 mg, 3.49 mmol), and DIPEA (2.25 g, 17.45 mmol) in DMF (50 ml) was added HATU (1.592 g, 4.19 mmol). The solution was allowed to stand at RT for 2 h and the DMF was evaporated. The residue was partitioned between EtOAc (150 ml) and sat. aqueous NaHCO3 (200 ml). The organic layer was separated and the aqueous was extracted further with EtOAc (2 x 150 ml). The combined extracts were washed with water (200 ml), brine (100 ml), dried (Na2SO4) and evaporated. The crude product was purified on an lsolute SPE Si Il cartridge (20 g) eluting with 40-60% EtOAc in pentane and then 100% EtOAc to afford a cream solid.Yield: 1.59 g (86%)LC-MS (Method 3): Rt 3.06 min, m/z 553 [MNa]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-3,3-diethoxypropane, and friends who are interested can also refer to it.

Reference:
Patent; ARGENTA DISCOVERY LTD.; WO2006/136857; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene, 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 202865-80-3, SDS of cas: 202865-80-3

Potassium acetate (10.52 g, 107.2 mmol) and bis(pinacolato)diboron (15 g, 58.96 mmol) were added to a solution of intermediate 7 (10.52 g, 107.2 mmol) in dioxane (125 ml), and the solution was degassed for 30 min. [1,1′-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) CH2Cl2 (4.4 g, 5.36 mmol) was added under nitrogen atmosphere and heated to 80 C. After 12 hours, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as a yellow oil (13.9 g, 99%) which was used without purification in the next step.

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

Reference:
Patent; TG THERAPEUTICS, INC.; RHIZEN PHARMACEUTICALS SA; LABORATOIRE FRANCAIS DU FRACTIONNEMENT ET DES BIOTECHNOLOGIES; Weiss, Michael S.; Miskin, Hari P.; Sportelli, Peter; Vakkalanka, Swaroop K.V.S.; US2015/290317; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, 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 1758-46-9, Computed Properties of C8H11NO

General procedure: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 349-55-3

EXAMPLE 68 Synthesis of 2-[(3-methoxy-5-(trifluoromethyl) phenyl)amino]phenylacetic Acid In the manner described in example 3, 2-bromophenylacetic acid is condensed with 3-methoxy-5-(trifluoromethyl)aniline to yield 2-[(3-methoxy-5-(trifluoromethyl)phenyl)amino]phenylacetic acid.

According to the analysis of related databases, 349-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Exocell, Inc.; US6355680; (2002); B1;,
Ether – Wikipedia,
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Application of 363-47-3, These common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, 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 glacial acetic acid (4.0 mL) precooled to 5 C were added potassium thiocyanate (4.0 mmol) and 2,6-difluoro-p-anisidine (1) (1.0 mmol). The mixture was stirred vigorously while 1.1 mmol of bromine in 1.5 mL of glacial acetic acid was added drop-wise such that the temperature did not rise beyond 0 C. After all the bromine was added (60 min), the solution was stirred for another 2 h at 0 C and at ambient temperature for 10 h. It was allowed to stand overnight, during which a yellowish-orange precipitate settled out. Water (30 mL) was added and the solution was adjusted to pH 6 with sat aq NaHCO3. The mixture was extracted with dichloromethane (3 × 50 mL) and the combined extracts were dried over Na2SO4 and evaporated to give a yellowish-orange solid as the crude product. Flash chromatography using hexane:dichloromethane 2:3 gave a dark yellow solid in 56% yield.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pirrung, Michael C.; Biswas, Goutam; De Howitt, Natalie; Liao, Jiayu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 20; (2014); p. 4881 – 4883;,
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These common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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. Computed Properties of C7H8BrNO

(w) By proceeding in a similar manner to Reference Example 4(a), method A, but using cyclopropyl cyanide and 5-bromo-2-methoxyaniline (Reference Example 50), there was prepared 1-bromo-3-(cyclopropyl-imino-methylamino)-4-methoxybenzene.

The synthetic route of 5-Bromo-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer Limited; US6303600; (2001); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem