Author: Jessica.F

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;,
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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;,
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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;,
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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;,
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Related Products of 150-78-7, 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. 150-78-7, name is 1,4-Dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Examples 17 to 44 show the versatility of the method with diferent compounds (0203) ALKYLCOMPSUBST and FCLALKYLHALIDES, they were done in analogy to example 1 , reaction conditions were 0.2 mmol of FCLALKYLHALIDE, CAT was Pt/C (Pt: 5 mol % relative to FCLALKYLHALIDE) and Cs2C03(l molar equivalent based on (0204) FCLALKYLHALIDE). ALKYLCOMPSUBST was used in the amount of 0.5 mL in case of a ALKYLCOMPSUBST being liquid and 1 mmol in case of ALKYLCOMPSUBST being solid, reaction was done under N2 atmosphere at 10 bar. Yield is isolated yield, in example 28 the yield was determined with 19F NMR with

The synthetic route of 1,4-Dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONZA LTD; TAESCHLER, Christoph; BELLER, Matthias; NEUMANN, Helfried; HE, Lin; NATTE, Kishore; ELLINGER, Stefan; ZARAGOZA DOERWALD, Florencio; WO2015/185677; (2015); A1;,
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These common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)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. COA of Formula: C11H15BrO

. A suspension of NaH (60% in mineral oil, 440 mg, 14 mmol) in DMF [(50] ml) was slowly added to a stirred solution of benzyl-4-bromobutyl ether (3.33g, 13.7 mmol) and amide 26 (5.41 g, 5.48 mmol) (WO 00/66587) in DMF (100 ml) kept at [5C.] The reaction mixture was stirred for 10 h at [50] C, quenched with 5 ml of H20 at [0] C, and evaporated to dryness in vacuo. The residue was taken up in ethyl acetate, washed with [H20,] and purified on a silica gel column using ethyl acetate/hexane: 3/7 as eluant; [5.] [1G, (81%)] of 27 were obatained [;’H-NMR] (CDCl3) : 0.97 (t, J=7. 1 Hz, 3H), 1.2-1. 5 (m, 16H), 2.27 (s, 3H), 2.29 (s, 9H), 2.55 (s, 24H), 2.9-3. 2 (m, 16H), 3.31 (t, J=6.0 Hz), 4.41 (s, 2H), 6.9-7. 0 (m, 8H), 7.2- 7.4 (m, [5H).]

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

Reference:
Patent; SLIL BIOMEDICAL CORPORATION; WO2004/2991; (2004); A1;,
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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. 22236-08-4, name is 3-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 22236-08-4

Intermediate 37 rac-Allyl [ 1 – {N’-cyano-N- [3 -(difluoromethoxy)phenyl] carbamimidoyl }-3-(3 ,4-dichloroph( dihydro-l/7-pyrazol-4-yl]methylcarbamate To a stirred solution of w-difluoromethoxy aniline, 10.1 g (6.35 mmol) in anhydrous tetrahydrofuran (30 mL) at -60 C under a nitrogen atmosphere was added lithium diisopropylamide, 3.2 l. (6.35 mmol, 2 M in tetrahydrofuran) . The reaction mixture was stirred for 30 min at -60 C before adding rac- phenyl 4-{[(ailyioxy)carbonyl](methyl)amino}-N-cyano-3-(3,4-dichiorophenyl)-4,5-dihydro-lH- pyrazole- 1 -carboximidate (intermediate 36) 1.0 g (2.12 mmol), in tetrahydrofuran (10 mL). The reaction mixture was stirred for 30 min at -60C and 1 h at room temperature. The reaction mixture was quenchend with water, then poured into brine and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by column chromatography on a NH- silica phase (eluent: hexane/ethyl acetate) to yield rac-allyl [1-{Nu’- cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH- pyrazol-4-yl]methylcarbamate, 875 mg (77%) as a beige oil. LCMS (method 2): R, = 1.36 min MS (ESI): [M + Hf = 536.8

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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2688-84-8, name is 2-Phenoxyaniline, 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. Application In Synthesis of 2-Phenoxyaniline

General procedure: The mixture of intermediate Bn-2 (1 eq.), p-toluenesulfonic acid monohydrate (PTSA*H2O) (172.5 g, 3 eq) in acetonitrile (ACN)(224 ml, 1.3 M) was cooled to 5 C. by using an ice bath. Sodium nitrite (NaNO2)(41.7 g, 2 eq.) in 240 ml water was added dropwise. After the addition was finished, the mixture was kept at 5 C. 1 hr. The resulting diazonium salt was treated slowly with potassium iodide (KI) (100 g, 2 eq.) in 300 ml water. After the completion of the reaction, the residue was extracted with EA and the combined organic layer was washed with a 10% Na2SO3(aq) and then dried over Na2SO4. The organic layer was concentrated under reduced pressure after filtration. The crude mixture was purified by silica-gel column chromatography to obtain intermediate Bn.

The synthetic route of 2688-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NICHEM FINE TECHNOLOGY CO., LTD.; LU, Tai-Ni; WU, Hui-Ling; SHIEH, Shwu-Ju; CHEN, Chi-Chung; (108 pag.)US2019/92745; (2019); A1;,
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