Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 450-88-4, name is 1-Bromo-4-fluoro-2-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 450-88-4, category: ethers-buliding-blocks

4-Fluoro-2-methoxybenzenethiol To a suspension of 2-bromo-5-fluoroanisole (2.00 g, 9.755 mmol) and elemental sulphur (0.468 g, 14.632 mmol) in dry THF (50 mL) was slowly added tert-butyl lithium in pentane (1.7 M, 12.6 mL, 21.46 mmol) AT-78C. The resulting suspension was allowed to stir at-78C for 60 mins before being poured onto saturated ammonium chloride solution (80 mL) and product extracted with diethyl ether (100 mL). The organic phase was washed with aqueous hydrochloric acid (2 N, 40 mL), with the resulting organic phase being dried (MgSO4) and the solvent evaporated in vacuo to give a pale yellow oil. This was treated to a pad of silica gel, eluting with hexane: ethyl acetate [95: 5] to give a pale yellow oil (1.50 g, 68%). ON (300 MHz, CDC13) 7.20 (1H, dd, Ar), 6.65-6. 55 (2H, d, AR), 3.90 (3H, s, OCH3), 3.68 (1H, s, SH).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/43903; (2004); A1;,
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Reference of 7025-06-1, These common heterocyclic compound, 7025-06-1, name is 1-Bromo-2-phenoxybenzene, 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.

37A. (1-(2-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate To a -78° C. solution of 1-bromo-2-phenoxybenzene (283 mg, 1.136 mmol) in anhydrous THF (5 mL) was added dropwise n-BuLi (545 muL of a 2.5 M solution in hexane, 1.363 mmol). The reaction was stirred at -78° C. for 0.5 h, after which a solution of 4-oxocyclohexane-1,1-diyl)bis(methylene)bis(4-methylbenzenesulfonate (1E; 530 mg, 1.14 mmol) in THF (4 mL) was added dropwise. The reaction mixture was slowly warmed to rt and stirred at rt for 2 h. Analytical HPLC showed the reaction was complete. Powdered NaOH (91 mg, 2.27 mmol) was added and the mixture was stirred under reflux for 18 h. The reaction was cooled to rt, diluted with water and extracted with EtOAc (2*). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude oil purified by flash chromatography (SiO2) using a gradient from 0percent to 40percent EtOAc/hexane (15 min) to give the title compound (230 mg, 0.495 mmol, 44percent yield) as a white solid. LCMS [M+H]+=465.1; 1H NMR (CDCl3) delta: 7.85-7.77 (m, 2H), 7.76-7.69 (dd, J=7.9, 1.9 Hz, 1H), 7.41-7.30 (m, 4H), 7.20-7.14 (td, J=7.6, 1.9 Hz, 1H), 7.14-7.06 (m, 2H), 6.98-6.92 (dd, J=7.6, 1.5 Hz, 2H), 6.83-6.76 (dd, J=8.1, 1.4 Hz, 1H), 3.87 (s, 2H), 3.75 (s, 2H), 2.59-2.50 (ddd, J=13.5, 11.3, 4.1 Hz, 2H), 2.48 (s, 3H), 1.98-1.87 (m, 2H), 1.75-1.64 (td, J=11.3, 10.8, 2.7 Hz, 2H), 1.60-1.51 (m, 2H).

The synthetic route of 7025-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang, Hao; Cheng, Peter T.W.; Chen, Sean; Tao, Shiwei; Wu, Shung C.; Negash, Lidet A.; US2014/275173; (2014); A1;,
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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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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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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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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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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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Electric Literature of 450-88-4, 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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate Example Int17.031 -(4-bromo-3-methoxyphenyl)-4-ieri-butylpiperazineTo a stirred solution of 1 -tert-butylpiperazine (5.0 g) in THF (25 mL) was added n-butyllithium in hexanes (4.2 mL, c = 2.5 M) at -78C. The solution was stirred for 30 min at 0C. A solution of 1 -bromo-4-fluoro-2-methoxybenzene (1.44 g) in THF (2 mL) was added at -78 C and the reaction mixture was allowed to warm up to 0 C over 3 h. The mixture was stirred at 0 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica-gel chromatography gave 490 mg of the title compound.

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

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; BRIEM, Hans; WO2012/160029; (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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Preparation 7; 4-(4-Methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamine; Tris(dibenzilideneacetone)dipalladium, 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 h. 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 water (1 x 100 mL). The organic phases were dried over anhydrous Na2SU4, 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. MS calc: 276.1318; MS found: 276.1320

The synthetic route of 886762-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; WO2009/156315; (2009); A1;,
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Electric Literature of 19056-40-7, A common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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 suspension of 4-bromo-3-methoxyaniline (2.5 g, 12.4 mmol) and potassium phosphate, tribasic (1.08 g, 6.19 mmol) in acetonitrile (40 mL) at 0°C, was added 2,4- dibromobutyryl chloride (1.64 mL, 12.4 mmol). The mixture was brought to rt and stirredfor 1 h. Aqueous NaOH (50percent) (5 mL, 12.37 mmol) was added, and the mixture was stirred at rt for 4 h. The reaction mixture was filtered through CELITE®, which was rinsed with acetonitrile. The filtrate was concentrated. The product was purified by flash chromatography (0-50percent EtOAc/Hex gradient) to obtain Intermediate 4 (3.5 g, 66percent yield) as a pinkish colored solid. MS(ESI) m/z: 350.0 (M+H) ?H NMR (300 MHz, chloroform-d) oe ppm 7.77 (d, J=2.27 Hz, 1 H) 7.53 (d, J=8.69 Hz, 1 H) 6.82 (dd, J=8.69, 2.27 Hz, 1 H) 4.61 (dd, J=7.18, 3.40 Hz, 1 H) 4.05 (dt, J=9.73, 7.22 Hz, 1 H) 3.94 (s, 3 H) 3.85 (ddd, J10.01, 7.55, 2.83 Hz, 1 H) 2.69 – 2.83 (m, 1 H) 2.48 (ddt, J=14.35, 6.70, 3.26, 3.26 Hz, 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; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; BODAS, Mandar Shrikrishna; YADAV, Navnath Dnyanoba; PATIL, Sharanabasappa; RAO, Prasanna Savanor Maddu; THIYAGARAJAN, Kamalraj; MAISHAL, Tarun Kumar; (498 pag.)WO2016/144936; (2016); A1;,
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