Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, 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 261762-35-0, name: 5-Bromo-1,2-difluoro-3-methoxybenzene

A solution of 1-bromo-3,4-difluoro-5-methoxy-benzene (1.11 g, 5.0 mmol, 1.0 eq.) and sodium methoxide (405 mg, 7.5 mmol, 1.5 eq.) in DMA (5 mL) is heated at 100C for lh. The reaction mixture is then poured into 60 ml. of water and ice, stirred and the resulting solid is filtered and dried under suction to afford the expected product.

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, 5-Bromo-1,2-difluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DE CEUNINCK, Frederic, Andre; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (147 pag.)WO2017/211667; (2017); 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, A new synthetic method of this compound is introduced below., Safety of 3,5-Dimethoxyphenylacetylene

To a solution of 1.5 g (9.2 mmol) of 1-ethynyl-3,5-dimethoxybenzene and 2.16 g (9.2 mmol) of 4-iodoanisole in 10.0 mL of pyrrolidine, 64 mg (0.246 mmol) of triphenylphosphine and 27 mg (0.123 mmol) of Pd(OAc)2 were added. The mixture was stirred under an Ar stream and heated at reflux temperature for 1.0 h. The mixture was frozen and poured into 60 mL of saturated ammonium chloride solution and then extracted with 30 mL of CH2Cl2. The organic layer was washed with brine and dried (Na2SO4). After filtration, the residue was purified by flash column chromatography on silica gel, with hexane-EtOAc, 9:1 as the eluent, to give pure (4) in 93% yield.

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lara-Ochoa, Francisco; Sandoval-Minero, Leticia C.; Espinosa-Perez, Georgina; Tetrahedron Letters; vol. 56; 44; (2015); p. 5977 – 5979;,
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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. 707-07-3, name is (Trimethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C10H14O3

Diol 25 (619 mg, 0.600 mmol) and 10-camphorsulfonic acid (12 mg, 0.05 mmol) were dissolvedin anhydrous CH2Cl2 (8.4 mL) under argon atmosphere, and trimethyl orthobenzoate (0.72 mL,0.76 g, 4.2 mmol) was added with stirring. After 16 h stirring at 20-23 C TLC (toluene-Me2CO7 : 3 v/v) showed incomplete reaction. Anhydrous Py (0.050 mL, 49 mg, 0.62 mmol) was thenadded, the volatiles were distilled off on a rotary evaporator (bath temperature 50 C), and theresidue was co-evaporated with toluene (3 × 10 mL, bath temperature 50 C). The resultingsyrup was dissolved again in anhydrous CH2Cl2 (8.4 mL) under argon atmosphere, and trimethylorthobenzoate (0.72 mL, 0.76 g, 4.2 mmol) and 10-camphorsulfonic acid (12 mg, 0.05 mmol)were added with stirring, and the solution was stirred at 23 C for 1 h (the reaction is completeaccording to TLC). Then Py (0.050 mL, 49 mg, 0.62 mmol) was added, and the volatiles weredistilled off on a rotary evaporator (bath temperature 50 C). The residue was suspended in amixture of AcOH (12 mL) and water (3 ml), heated until all the solids dissolved (~60 C) and themixture was stirred at 20-23 C for 20 h. Then the solution (containing a small amount of anamorphous precipitate) was concentrated under reduced pressure, the residue was co-evaporated with water (15 mL), then with toluene (15 mL), the resulting yellowish syrup was dissolved intoluene (20 mL) and washed with 1 M aq Na2CO3 (10 mL). The aqueous layer was backextractedwith toluene (3 × 5 mL). The combined organic phases were dried (Na2SO4) andconcentrated under reduced pressure. The resulting syrup was purified by columnchromatography on silica gel (gradient 5?33% EtOAc in toluene). The fractions containg themain product were pooled, concentrated under reduced pressure, and the residue (white foam,610 mg) was lyophilized from benzene (10 mL) (Caution Benzene is a proven carcinogen) togive the 3-hydroxy derivative (590 mg, 87%) as a light, very brittle white amorphous 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:
Article; Abronina, Polina I.; Zinin, Alexander I.; Malysheva, Nelly N.; Stepanova, Elena V.; Chizhov, Alexander O.; Torgov, Vladimir I.; Kononov, Leonid O.; Synlett; vol. 28; 13; (2017); p. 1608 – 1613;,
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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. 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H9BrO2

n-BuLi (2.5 M in THF, 3.3 mL, 8.3 mmol) was added drop wise to a stirred solution of 1-bromo-2,4-dimethoxybenzene (7) (1.5 g, 6.9 mmol) in THF (15 mL) at -78 °C under N2 atmosphere. After 30 min, CO2 gas was passed through the solution during 45 min of time and the mixture was allowed to warm up to room temperature. THF was removed in vacuum and the mixture was treated with saturated NaHCO3 solution (40 mL). The water layer was washed with ethyl acetate (2*20 mL) and then acidified with conc. HCl. The mixture was extracted with ethyl acetate (2*75 mL). The organic layer was washed with water (2*30 mL), brine (30 mL), dried (Na2SO4), filtered and concentrated. Recrystallization from ethyl acetate produced 9 (1.15 g, 91percent) as white solid. Rf 0.3 (1:1 ethyl acetate:hexane); mp 103-105 °C (lit.22 107-109 °C); 1H NMR (CDCl3, 500MHz): delta 8.10 (d, 1H, J=9.0Hz, C6-H), 6.61 (dd, 1H, J=9.0, 2.0Hz, C5-H), 6.50 (d, 1H, J=2.0Hz, C3-H), 4.01 (s, 3H, OMe), 3.86 (s, 3H, OMe); 13C NMR (CDCl3, 125MHz): delta 179.9 (C), 165.2 (C), 160.2 (C), 135.2 (CH), 110.1 (C), 106.2 (CH), 98.5 (CH), 56.4 (CH3), 55.7 (CH3).

The synthetic route of 17715-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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Related Products of 888327-32-0, 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. 888327-32-0, name is 4-Bromo-1-(difluoromethoxy)-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 77 Preparation of: 2-amino-5-[4-(difluoromethoxy)-3-methylphenyl]-3-methyl-5-(3-methylphenyl)- 3,5-dihydro-4H-imidazol-4-oneStep 1 : 1-(difluoromethoxy)-2-(2-fluoroethyl)-4-(phenylethvnyl)benzene; In a 50 mL round-bottomed flask was placed 4-bromo-1-(difluoromethoxy)-2- methylbenzene (0.8 g, 3.37 mmol) and DMF (6.75 mL) was added to give a colorless solution.1-Ethynyl-3-methylbenzene (0.436 mL, 3.37 mmol) and triethylamine (2.352 mL, 16.87 mmol) were added. The reaction was degassed by bubbling with N2.Bis(triphenylphosphine)palladium(ll) chloride (0.118 g, 0.169 mmol) was added and N2 bubbling was continued. Copper iodide (0.032 g, 0.169 mmol) was added. The reaction was heated to 60 C for 12h. The reaction was cooled and partitioned between ether (70 mL) and 1MHCI (50 mL). The organic was washed with 1 M HCI (50 mL) and brine (2 x 50 mL). The organic layer was dried over Na2SO4. The crude was purified by flash chromatography (100% hexanes) to provide 1-(difluoromethoxy)-2-methyl-4-(m-tolylethynyl)benzene (0.88 g, 3.23 mmol, 96% yield) as a yellow oil with minor impurities.1H NMR (400 MHz, DMSO-d6) § 7.05-7.70 (m, 7H), 7.18 (t, JH.F = 74 Hz, 1H), 2.30 (s, 3H), 2.20(s, 3H)

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

Reference:
Patent; WYETH; WO2008/115552; (2008); A1;,
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Reference of 707-07-3,Some common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, molecular formula is C10H14O3, 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: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Trimethoxymethyl)benzene, its application will become more common.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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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 1579-40-4 as follows. category: ethers-buliding-blocks

Chlorosulfonic acid diluted (14.11g, 121.1mmol) in dichloromethane 30ml, was cooled in an ice water bath to 5 .This solution, di (para-tolyl) ether (10.0g, 50.44mmol) in dichloro-methane and then added dropwise to a solution (20ml), The reaction solution is warmed to room temperature was stirred for 2 hours.Was added dropwise distilled water (10ml) to the reaction solution was distilled off dichloromethane to the evaporator.Dropping the resulting solution into a saturated sodium chloride solution of 500ml, and then recovering the resultant precipitate was separated by filtration, and was dissolved by heating in distilled water 400ml.By cooling in ice water and this solution was filtered recovering the resulting precipitate.The resulting solid was dissolved in 50ml of methanol and adding Amberlite IR120 be small (Aldrich Co.) 20g, were stirred at room temperature for 30 minutes.Next, the reaction solution was filtered, concentrated by drying the obtained filtrate, to give a compound A1-1 (4.7g, 14.23mmol)

According to the analysis of related databases, 1579-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG CHEMICAL CO., LTD; PARK, JONG HO; SAH, KONG CHUN; KIM, SUNG HYUN; BAEK, GYUNG LIM; RYU, CHANG HYUN; (91 pag.)KR2015/128789; (2015); A;,
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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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

Preparation of compound (6); A solution of (S)-(+)-Z-4- amino-2-hydroxybutyric acid (5) (5 g, 19.74 mmol) in toluene (38 mL) containing N,N-dimethylformamide di-tert-butyl acetal (18.92 mL, 78.96 mmol) was heated to 95C for 3 h. The solvent was then evaporated and the crude product was purified by flash chromatography on silica gel (n-hexane/EtOAc = 7:4) to give (6) (3.4 g, 55.7 % yields) as yellow solid. Mp 42-44C; [alpha]20D= – 5.9 (c= 10.1 mg/ml, CHC13) 1H-NMR (CDCl3) delta: 1.47 (s, 9H); 1.76-1.85 (m, 1H); 1.94-2.09 (m, 1H); 2.74 (br s, 1H); 3.36 (dd, J= 6.04 Hz, J= 11.99 Hz, 2H); 4.10 (dd, J= 4.02 Hz, J= 8.05 Hz, 1H); 5.09 (s, 2H); 5.21 (br s, 1H); 7.31-7.37 (m, 5H) Anal. Calcd. for C16H23NO5: C, 62.12; H, 7.49; N, 4.53. Found: C, 62.22; H, 7.48; N, 4.53.

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 36805-97-7.

Reference:
Patent; Bracco S.P.A.; EP1972617; (2008); A1;,
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Reference of 1515-81-7, A common heterocyclic compound, 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, molecular formula is C9H12O2, 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: The reactions were carried out a ~40 mL, Teflon-lined, stainlesssteelautoclave. AcOH (2 mL), TEMPO (0.25 mmol), HNO3 (0.25mmol), the appropriate benzylic methyl ether (0.5 mmol), andNH4OAc (1.5 mmol) were added sequentially to the autoclave.Subsequently, the autoclave was pressurized to 1 MPa with O2,and the reaction mixture was heated with magnetic stirring at50 C for 20 h, then cooled to r.t. The mixture was then dilutedwith Et2O (15 mL) and H2O (5 mL), and adjusted to pH 7-8 with2 M aq NaOH. The two layers were separated, and the aqueouslayer was extracted with Et2O (3 × 15 mL). The organic layerswere combined, dried (Na2SO4), filtered, and concentrated to avolume of approximately 3 mL in a rotary evaporator. GC analysisof the concentrated organic phase, with biphenyl or 1,2,4,5-tetramethylbenzene as internal standard, provided the GC yieldof the product. The crude product in the concentrated organicphase from another parallel experiment was purified bycolumn chromatography [silica gel (200-300 mesh), EtOAc-PE].

The synthetic route of 1515-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Xinzhe; Ren, Yun-Lai; Ren, Fangping; Cheng, Xinqiang; Zhao, Shuang; Wang, Jianji; Synlett; vol. 29; 18; (2018); p. 2444 – 2448;,
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Electric Literature of 25245-34-5,Some common heterocyclic compound, 25245-34-5, name is 2-Bromo-1,4-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.

EXAMPLE 214 1,2-Dihydro-9-methoxy-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 314, structure 41 of Scheme XI, where R1 =H, R2 =methoxy) 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,4-dimethoxybenzene, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;,
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