Month: July 2021

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. 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Product Details of 887581-09-1

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

The synthetic route of 887581-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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Electric Literature of 36865-41-5, A common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 stirred solution of 3-hydroxy-4-methoxybenzaldehyde (40 g,0.17 mol) in MeCN (500 ml) were added 1-bromo-3-methoxypropane (32 g, 0.21 mol) andK2C03 (70 g, 0.51 mol). The mixture was refluxed overnight, cooled to room temperatureand quenched with H20, and extracted with Et0Ac(1 00 ml x 3). The combined organiclayers were washed with brine, dried over Na2S04, and concentrated to give crude 4-methoxy-3-(3-methoxypropoxy)benzaldehyde (50 g, 84% yield) as a white solid. LCMS(ESI) m/z: 225.3 (M + 1t.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); 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 16618-68-1 as follows. HPLC of Formula: C7H8BrNO

c) A solution of the compound of Example 374(b) (1 g, 4.78 mmol, 1.2 eq.), 3-bromo-5-methoxyaniline (0.8 g, 3.98 mmol) and potassium fluoride (0.23 g, 3.98 mmol, 1 eq.) in DMF was heated at 120 C. for 12 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane) to give the product in 42% yield (0.81 g).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (2015); A1;,
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These common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)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. Product Details of 886762-08-9

Preparation F-(4-Methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamine.Pd2(dba)3 (1.1 g, 1.2 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (0.94 g, 2.4 mmol), 5- bromo-2-trifluoromethoxy-phenylamine (30.7 g, 120 mmol) in THF (50 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (1 M in THF, 288 mL) and N-methylpiperazine (26.7 mL, 194 mmol) were added and the reaction refluxed for 1 hours. The reaction mixture was then allowed to cool to room temperature and filtered through a pad of celite. The organic phase was concentrated, the residue dissolved in DCM (200 mL) and washed with H2O (1 x 100 mL). The organic phases were dried over anhydrous Na2S04, the solvent evaporated in vacuo and the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 23 g of 4-(4-methyl-piperazin-1-yl)-2- trifluoromethoxy-phenylamine (70% yield) as a light brown powder.1H NMR (401 MHz, DMSO-d6) delta ppm 2.22 (s, 3H), 2.44 (t, J=4.88 Hz, 4H), 2.94 (t, J=4.88 Hz, 4 H) 4.77 (br.s., 2 H) 6.66-6.69 (m, 1 H) 6.73 – 6.80 (m, 2 H);MS calc: 276.1318; MS found: 276.1320

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

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; CALDARELLI, Marina; BERIA, Italo; COLOMBO, Nicoletta; PIUTTI, Claudia; SALSA, Matteo; TRAQUANDI, Gabriella; WO2012/13557; (2012); 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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H25NO2

Example 3; Ethyl 6-[(dimethylamino)methylene]-l-methyl-7-oxo-4,5,6,7-tetrahydro-lH- indazole-3-carboxylate; 16 g (72 mmol) of ethyl l-methyl-7-oxo-4,5,6,7-tetrahydro-lH-indazole-3- carboxylate were dissolved in 100 mL of dimethylformamide and 32 mL of dimethylformamide ditertbutyl acetale were added. The mixture was stirred at 600C for 8 hours. The solvent was then evaporated in vacuo and the product crystallized from ethanol to give the title compound (17.96 g, 90 % yield). 1H NMR (400 MHz, DMSO-J6) delta ppm 1.31 (t, J= 7.07 Hz, 3 H) 2.83 (m, 2 H) 2.92 (m, 2 H) 3.13 (s, 6 H) 4.14 (s, 3 H) 4.24 (q, J= 7.07 Hz, 2 H) 7.49 and 7.52 (2 s, 1 H).

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; NERVIANO MEDICAL SCIENCES S.r.l.; WO2008/74788; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 20469-65-2, These common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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.

Example 19 Synthesis of (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene To a stirred solution of 1-bromo-3,5-dimethoxybenzene (35) (2.17 g, 10.0 mmol) in THF (50 mL), cooled to -78 C., and n-BuLi (12.5 mL, 1.6 M in hexane, 20.0 mmol) was added dropwise. The mixture was allowed to warm to -20 C. over 2.5 h. The reaction was diluted with EtOAc (300 mL) and washed with water (150 mL). The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 2:1) gave 1-iodo-3,5-dimethoxybenzene (36) (1.6 g, 60%) as a brown oil.

Statistics shows that 1-Bromo-3,5-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 20469-65-2.

Reference:
Patent; Aquinox Pharmaceuticals Inc.; US2011/136802; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

589-10-6, name is (2-Bromoethoxy)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of (2-Bromoethoxy)benzene

General procedure: To a solution of 1 (200 mg, 0.27 mmol) and K2CO3 (55 mg, 0.40 mmol) in DMF (5 mL), the corresponding bromoalkane derivative 2 or 3 (0.33 mmol) was added under a nitrogen atmosphere and the mixture was stirred at 90C. After the completion of the reaction, water (50 mL) was added and the product was extracted with ethyl acetate (20 mL×3). The combined organic phase was dried over anhydrous Na2SO4. The crude mixture was chromatographed over silica gel column using a mixture of ethyl acetate and petroleum ether. P5-C2-Ph: white solid, in 85.6 %, m.p. 130~131 C; IR (KBr) nu/cm-1: 3050 (C=C-H), 2936, 2853, 2830 (C-H), 1600, 1497, 1469 (Ar-C=C), 1212, 1048 (C-O); 1H NMR (600 MHz, CDCl3) delta/ppm: 7.32 – 7.30 (m, 2H, C3-H,C5-H), 6.98 – 6.96 (m, 3H, C2-H, C6-H, C4-H), 6.82-6.77 (m, 10H, Ca-H), 4.27 (t, J = 6.0 Hz, 2H, C8-H), 4.15 (t, J =6.0 Hz, 2H, C7-H), 3.82 (m, 10H, Cb-H), 3.68 -3.65 (m, 24H, Cc-H), 3.56 (s, 3H, Cc-H); 13C NMR (151 MHz, CDCl3) delta/ppm: 158.95 (C-1), 151.41, 150.93, 149.82, 129.66, 128.35, 116.08, 114.82, 114.27, 114.23, 114.20, 114.13, 114.10 (C-a), 129.24 (C-3,C-5), 121.18 (C-4), 114.41 (C-2,C-6), 67.88 (C-8), 67.08 (C-7), 55.99, 55.97, 55.95, 55.92, 55.90, 55.87, 55.86, 55.77, 53.03 (C-c), 32.02 , 29.86, 29.81, 29.73, 29.68, 22.79, 14.25 (C-b); ESI-MS m/z : 856.61 ([M]+), 874.74 ([M+NH4]+), 879.75([M+Na]+); HRESI-MS m/z : calcd for C52H56O11 856.3823, found 857.3876 ([M+H]+).

The synthetic route of 589-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Lu-Zhi; Hua, Zhong-Ze; Duan, Wen-Gui; Huang, Hong-Fei; Huang, Yan; Lin, Gui-Shan; Cen, Bo; Tetrahedron Letters; vol. 57; 27-28; (2016); p. 2969 – 2971;,
Ether – Wikipedia,
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Related Products of 1978-39-8, These common heterocyclic compound, 1978-39-8, name is 5-Fluoro-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.

a) 4-fluoro-2-isocvanato-1 -methoxybenzene5-fluoro-2-methoxyaniline (5.0 g, 35 mmols) was dissolved in dioxane (70 mL) and a solution of trichloromethyl chloroformate (2.11 mL) in the same solvent (20 mL) was added dropwise. It was stirred at 6O0C for 20 hours. It was concentrated in vacuo and diethyl ether was added. The solid precipitated was filtered off and the mother liquors were concentrated in vacuo to give the title compound (4.66 g).

The synthetic route of 1978-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL PRODESFARMA, SA; WO2006/133802; (2006); A1;,
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Electric Literature of 7025-06-1, 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. 7025-06-1, name is 1-Bromo-2-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

The 1-bromo-2-phenoxybenzene 0.018 muM is dissolved in 100 ml, in dry THF, added after the never-dried 500 ml three-mouth bottle, N2 -78 °C under the protection of the reaction 30min, slow adds by drops positively BuLi 0.027 muM, after dropping maintain -78 °C reaction 3h, then slowly dropping triisopropyl borate 0.02 muM, after dropping the reaction is maintained in the -78 °C reaction 2h, slow heating to room temperature, the reaction overnight, TLC monitoring after the reaction is completed, water slow quenching the reaction solution, extraction to dryness, to obtain 2-phenoxyphenylboronic acid (B-1) 0.0144 muM, and the yield is 80percent. Mass spectrum: 214.06.

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

Reference:
Patent; Jilin Optical and Electronic MaterialsCo.,Ltd; Cui, Dunzhu; Wang, zhao; Bi, Yan; Qin, Cuiying; Hu, Xiaoming; Gao, Chunji; (43 pag.)CN106565434; (2017); A;,
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Application of 103291-07-2, 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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 2 2-(4-Fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane; Anhydrous 1,2-dimethoxy ethane (12 mL) was added to 4-bromo-l-fiuoro-2- methoxybenzene (1.02 g, 5.0 mmol), tris(dibenzylideneaceton)dipalladium (0) (228 mg, 0.25 mmol), tricyclohexylphosphine (209 mg, 0.75 mmol), potassium acetate (732 mg, 7.5 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-l,3,2-dioxaborolane (1.14 g, 4.5 mmol) and the resulting mixture was irradiated in a microwave at 150 C for 1 h. When cooled to ambient temperature the mixture was filtered and the solvent was evaporated in vacuo to give the crude product: MS (EI) m/z 252 [M+»]

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-fluoro-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/145568; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem