Author: Jessica.F

Reference of 1112210-82-8,Some common heterocyclic compound, 1112210-82-8, name is 1,3-Dibromo-5-isopropoxybenzene, molecular formula is C9H10Br2O, 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.

Synthesis of Intermediate 2)Molecular Weight: 293.98 Molecular Weight: 186.21[00530] In a 3-neck 100 mL round-bottomed flask, intermediate- 1 (3.5 g, 1 eq.) was dissolved in DMF and degassed it for 20-30 min. To this reaction mixture, Zinc Cyanide (1.72 g, 1.2 eq.) and tetrakis (0.705 g, 0.05 eq.) was added. Resulting reaction mixture was stirred at 80-90C and reaction was monitored by TLC using Ethyl acetate: hexane (1 :9) as mobile phase, which shows starting material was consumed after 5 h. Reaction was quenched into ice-water slurry and compound was extracted using ethyl acetate (50 mL x 3), combined organic layer were dried over anhydrous sodium sulfate and concentrated under reduce pressure to give crude compound. The crude material was subjected to column chromatography using silica 60/120 as stationary phase and ethyl acetate :n-Hexane as mobile phase. Compound was eluted in 7% ethyl acetate in Hexane. Fractions containing compound was distilled out using rotary evaporation at 40 C/250 mm Hg to obtain 2.095 g (94.51%). Mass/LCMS: LC-MS purity 92.36%, NMR: Confirmed.

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

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SHECHTER, Sharon; KAUFFMAN, Michael; SANDANYAKA, Vincent, P.; SHACHAM, Sharon; WO2011/109799; (2011); 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. 61367-43-9, name is cis-4-Methoxycyclohexanamine hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 61367-43-9

Compound 1a (60 mg, 0.44 mmol) was dissolved in NMP (1 mL) and was added cis-4-methoxycyclohexan-1-amine hydrochloride (62 mg, 0.51 mmol), DIPEA (114 mg, 0.88 mmol), then was stirred at 100 C for 16 hours. The reaction mixture was cooled to room temperature, and was added to water, extracted with CH2Cl2 (10 mL x 3). The combined organic phase was washed with brine (10 mL), dried over Na2SO4 and filtered, the filtrate was concentrated in vacuo, the crude product was purified via preparative TLC (CH2Cl2/MeOH= 10/1) to afford compound 3b (35 mg, yield 32%) as a pale yellow solid.

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; Hangzhou Innogate Pharma Co., Ltd.; ZHANG, Hancheng; LIU, Shifeng; YE, Xiangyang; (47 pag.)EP3483158; (2019); A1;,
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These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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. Application In Synthesis of 1-(Benzyloxy)-3-bromobenzene

Magnesium strip (1.29 g, 52.8 mmol) in anhydrous THF (50 mL)To the suspension was added iodine which was heated with magnesium.The mixture was refluxed and an approximately 5% solution of 3-bromobenzyl phenol(13.9 g, 52.8 mmol) was added.At the beginning of the reaction, the bromide solution is added dropwise and the mixture is then refluxed again1 hour. The mixture was cooled to about 5 C and a solution of cyclopentanone (4.44 g, 52.8 mmol) in THF (50 mL) was added dropwise. The mixture was stirred at rt for 72 h,The reaction was then quenched with a cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

The synthetic route of 1-(Benzyloxy)-3-bromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; KALAYANOV, GENADIY; TORSSEL, STAFFAN; WAHLING, HORST; (130 pag.)TW2018/15396; (2018); A;,
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Related Products of 18800-30-1, These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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 1-bromo-4-(2-bromoethoxy)benzene (19.9 g, 100 mmol; see step (a) above) in THF (120 mL) was portion-wise added t-BuOK (14.0 g, 125 mmol) over 10 min at 0C. After stirring at room temperature for 16 h, the mixture was diluted with ‘water (400 mL) and the product was extracted with light petrol (4×100 mL). The combined organic extracts were washed with brine, dried (Na(at)S04), concentrated and distilled under vacuum to yield the sub-title compound (11.5 g, 58%).

The synthetic route of 18800-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2005/123673; (2005); A1;,
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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 321-28-8 as follows. Quality Control of 1-Fluoro-2-methoxybenzene

1-Fluoro-2-methoxybenzene a13 (0.0126 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine ethyl ester b1 were added sequentially under argon protection. 0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 48 hours under a 6W blue light at room temperature.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 20/1.A yellow liquid (30) (0.0188 g, 95%) was obtained.

According to the analysis of related databases, 321-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
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Application of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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 mixture of 2,6-dichloropyrimidine (2.00 g, 13.4 mmol), 3-benzyloxoaniline (2.07 g, 13.4 mmol) and triethylamine (2.72 g, 26.8 mmol) in 1-butanol (20 mL) was stirred at 50¡ã C. for 17 h. The reaction mixture was concentrated to remove most of the 1-butanol, the crude product was preadsorbed onto silica gel using chloroform and purified by flash chromatography (95:5 chloroform/methanol) to afford N4-(3-benzyloxyphenyl)-2-chloro-4-pyrimidineamine (1.70 g, 40percent) as colorless oil: 1H NMR (300 MHz, DMSO-d6) delta 10.2 (s, 1H), 8.16 (d, J=6.0 Hz, 1H), 7.48-7.24 (m, 7H), 7.12 (d, J=9.0 Hz, 1H), 6.78 (m, 2H), 5.11 (s, 2H); ESI MS m/z 312 [C17H14ClN3O+H]+.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); A1;,
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Synthetic Route of 54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 9 Synthesis of 2,7-Dibromo-9,9-bis(3,6-dioxaheptyl)-fluorene Benzyltriethylammonium chloride (3.19 g, 14 mmole, 0.077 eq) and 2,7-dibromofluorene (59 g, 182 mmole, 1 eq) were suspended in 178 mL DMSO. 50% aqeous NaOH (80 mL) was added. 1-Bromo-2-(2-methoxyethoxy)ethane (80 g, 437 mmole, 2.4 eq) was then added in small portions. The reaction was stirred at room temperature for 2 hours before it was stopped and the aqueous layer was extracted with ether. The combined ether layers were washed with water five times and dried over Na2SO4. The organic layer was filtered, evaporated to dryness, and the residual was flash chromatographed on a silica-gel column to give 73 g of the pure compound in a yield of 86%.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-(2-methoxyethoxy)ethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; 3M Innovative Properties Company; US7094902; (2006); B2;,
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Electric Literature of 1758-46-9, 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. 1758-46-9, name is 2-Phenoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.137 g (1 mmol) of phenoxyethylamine, 1.0 mmol of triethylamine, Catalytic amount of 4-dimethylaminopyridine (DMAP), 20 mL of dichloromethane, 1.2 mmol of (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoyl chloride was added dropwise under ice bath The dichloromethane solution was dissolved in about 15 minutes and allowed to react at room temperature for 1 hour. After the reaction is completed, the organic layer is washed with water and washed with saturated brine. Dry, desolvent, The crude product was subjected to column chromatography [V petroleum ether: V ethyl acetate = 7:1 to 5:1] to afford white (R)-2-N-(2-phenoxyethyl)-2-[4-(6 -chloroquinoxaline-2-yloxy)phenoxy]propanamide, mp 150-153 C, yield 78.3%,

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

Reference:
Patent; Anhui Agricultural University; Tian Shengni; Yang Zihui; Ye Aihua; Huang Shixia; Li Junhong; Tian Qi; (8 pag.)CN108689921; (2018); A;,
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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, Application In Synthesis of 2-Phenoxyethylamine

General procedure: To a solution of 2-phenoxy-ethylamine (5 eq.) or 2-(2-methoxyphenoxy-)ethylamine (5 eq.) in 2-methoxyethanol(25 mL per mmol of amine) the appropriate aliphatic chloride33-39 (1 eq.) and KI (cat.) was added. The mixturewas refluxed for18-48 h and concentrated. The residue was suspended in CHCl3and washed with 1M NaOH, brine, dried over anhydrous Na2SO4and concentrated. The crude was purified by flash chromatographyto give the titled compound.4.1.2.1 2-(2,2-Diphenyl-1,3-dioxolan-4-yl)-N-(2-phenoxyethyl)ethan-1-amine (17) Pale yellow liquid (74% yield). TLC (cicloexane/EtOAc 3:7): Rf?=?0.38. 1H NMR (600?MHz, Chloroform-d) delta 1.71-1.76 (m, 1H), 1.83-1.89 (m, 1H), 1.98 (bs, 1H), 2.73-2.77 (m, 1H), 2.80-2.84 (m, 1H), 2.92 (t, J?=?5.1?Hz, 2H), 3.63 (t, J?=?7.5?Hz, 1H), 3.97 (t, J?=?5.1, 2H), 4.05 (t, J?=?7.2?Hz, 1H), 4.16-4.20 (m, 1H), 6.77-6.94 (m, 3H), 7.13-7.28 (m, 8H), 7.36-7.49 (m, 4H). 13C NMR (151?MHz, CDCl3) delta 33.65, 46.64, 48.85, 67.06, 70.02, 75.60, 114.54, 120.89, 126.20, 127.96, 128.05, 128.16, 129.48, 142.64, 158.78. MS (ESI): m/z [M + H]+: 389.2.

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

Reference:
Article; Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 310 – 325;,
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Synthetic Route of 17715-69-4,Some common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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 suspension of Pd2(dba)3 (6.9mg, 0.0075mmol), tBu3PHBF4 (8.7mg, 0.03mmol), KOH (42mg, 0.75mmol), aryl bromide 4 (0.36mmol) and tetralone 3 (0.3mmol) in a mixture of dioxane/water (4:1, v/v, 3mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100¡ãC, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography. Dioxane quality is extremely important for the success of the reaction. Characterization of alpha-aryl-alpha-tetralones is given in Ref.[26].

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-2,4-dimethoxybenzene, its application will become more common.

Reference:
Article; Fernandes, Talita de A.; Costa, Paulo R. R.; Manvar, Dinesh; Basu, Amartya; Kaushik-Basu, Neerja; Domingos, Jorge L. O.; Nichols, Daniel Brian; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 33 – 38;,
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