Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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 1462-37-9, Formula: C9H11BrO

Methyl 1-(2-(benzyloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate. Intermediate 4 (1.029 g, 4.0 mmol) was added to a suspension of NaH (192 mg of 60percent dispersion in mineral oil, 4.8 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 15 minutes, treated with benzyl 2-bromoethyl ether (0.7 mL, 4.4 mmol), stirred at room temperature for 2 hours, quenched with water, and extracted with ethyl acetate (2.x.50 mL). The organic layers were combined and washed (1N HCl), dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 3:1 hexanes/ethyl acetate) to provide the desired product as a colorless thick oil (1.19 g, 76percent yield). MS m/z 392(MH+); 1H NMR (500 MHz, CDCl3) delta 1.31 (m, 1H), 1.45 (m, 4H), 1.80 (d, J=13.12 Hz, 1H), 1.87 (m, 2H), 2.10 (m, 2H), 2.84 (m, 1H), 3.79 (t, J=5.34 Hz, 2H), 3.94 (s, 3H), 4.33 (t, J=5.49 Hz, 2H), 4.45 (s, 2H), 7.12 (s, 1H), 7.20 (m, 2H), 7.27 (m, 3H), 7.66 (d, J=8.55 Hz, 1H), 7.78 (d, J=8.55 Hz, 1H), 8.08 (s, 1H).

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

Reference:
Patent; Hudyma, Thomas W.; Zheng, Xiaofan; He, Feng; Ding, Min; Bergstrom, Carl P.; Hewawasam, Piyasena; Martin, Scott W.; Gentles, Robert G.; US2006/46983; (2006); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C10H13BrO

[(3-Benzyloxy-propyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester To an oven-dried flask was added 10.25 g (44.7 mmol) of (3-Bromo-propoxymethyl)-benzene and 7.67 mL (44.7 mmol) of triethyl phosphite. The flask was fitted with a short-path distillation head, for removal of bromoethane, and the mixture heated at 150¡ã C. for 4 h. The reaction was cooled to ambient temperature, and then diluted with 120 mL of absolute ethanol and 1.8 N KOH (120 mL, 216 mol). The distillation head was replaced with a reflux condenser and the solution heated at reflux for 5 h. The reaction was cooled then concentrated in vacuo. The basic aqueous layer was extracted with EtOAc (2*) and then acidified to pH 3 with conc. HCl. The aqueous layer was extracted with EtOAc (3*) and the combined extracts were dried over MgSO4 and concentrated. The resulting crude product (8.24 g) was used as is in the next reaction. 31P NMR (300 MHz, DMSO-d6) delta34.113.

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; Metcalf III, Chester A.; Shakespeare, William C.; Sawyer, Tomi K.; Wang, Yihan; Bohacek, Regine; US2003/114486; (2003); A1;,
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7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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. Recommanded Product: 7252-83-7

To a solution of o-thiocresol (16. 89g, 136mmo1) in acetone (130ml) is added potassium carbonate (20. 5g, 148mmol) and a solution of bromoacetaldehyde dimethylacetal (19.93g, 123mmol) in acetone (20ml) and the reaction mixture is stirred at ambient temperature overnight. The solids are filtered and washed with diethyl ether. The filtrate is concentrated and dissolved into ethyl acetate, washed successively with water, 0.5 N NaOH, and 2N NaOH. The combined aqueous fractions are extracted with dichloromethane. The combined organic fractions are dried over anhydrous MgS04, filtered and concentrated to afford 1- [ (2, 2-dimethoxyethyl) thio] -2-methyl-benzene as a brown oil (23.4g, 90%) that is used without further purification.’H NMR (CDC13) : 8= 7.33 (1H, brd), 7.19-7. 08 (3H, m), 4.56 (1H, t), 3.38 (6H, s), 3.10 (2H, d), 2.42 (3H, s).

The synthetic route of 7252-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/92885; (2005); A1;,
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Electric Literature of 134364-69-5,Some common heterocyclic compound, 134364-69-5, name is 2,3-Difluoroanisole, molecular formula is C7H6F2O, 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.

In a 1 L four-necked flask purged with nitrogen, 102 gOf 1, 2-difluoro-3-methoxybenzene was dissolved in 300 ml of THF and cooled to -78 C. To this was added 326 ml of a 2.4 M solution of butyllithium in hexane over 1 hour. After 1 hour, a solution of 133 g of trimethyl borate dissolved in 130 ml of THF was added dropwise over 1 hour. After 1 hour, the temperature of the system was brought to -30 C., 160 ml of 36% hydrochloric acid was added and the mixture was stirred for 2 hours. To the system, 500 ml of ethyl acetate and 200 ml of water were added and stirred, and the organic layer was separated. The mixture was further extracted with 200 ml of ethyl acetate and combined with the above organic layer, which was washed with 100 ml of saturated brine. After drying the solution with magnesium sulfate, the solvent was distilled off to obtain 133 g of the desired product as a white solid. Yield 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Difluoroanisole, its application will become more common.

Reference:
Patent; DIC CORPORATION; KUSUMOTO, TETSUO; AOKI, YOSHIO; (47 pag.)JP6136589; (2017); B2;,
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Related Products of 19500-02-8, 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 19500-02-8 as follows.

A solution of dimethyl acetylenedicarboxylate (17 g, 0.12 mol) in MeOH (20 mL) was added dropwise over 1 h to a solution of 3-methoxy-2-methylaniline (13.7 g, 0.1 mol) in MeOH (80 mL) stirred at r.t., and the mixture was stirred at r.t. for an additional 4 h. Evaporation of MeOH provided 7a (29.7 g; quantitative yield corresponds to 27.9 g) of yellowish oil (HPLC purity 93.5percent), which was used for the following step without further purification.

According to the analysis of related databases, 19500-02-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Radl, Stanislav; Rezkova, Hana; Obadalova, Iva; Srbek, Jan; B?icha?, Ji?i; Pekarek, Toma?; Synthesis; vol. 46; 7; (2014); p. 899 – 908;,
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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. 592-55-2, name is 1-Bromo-2-ethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2-ethoxyethane

1-Boc-piperazine (1.86 g, 10.0 mmol), 2-bromoethyl ethyl ether (1.92 g, 12.5 mmol) and K2CO3 (2.07 g, 15.0 mmol) in CH3CN (25 mL) were stirred at 70 C for 19 h. The mixture was allowed to cool to room temperature. The solids were filtered off and the filtrate was diluted with EtOAc (60 mL). The organic phase was washed with water (6 mL) and brine (6 mL), dried over Na2SO4, and evaporated to yield 2.45 g (95%) of tert-butyl 4-(2- ethoxyethyl)piperazine-1-carboxylate.1H NMR (600 MHz, DMSO-d6) delta ppm 3.46 (t, J=6.0 Hz, 2 H) 3.40 (q, J=7.0 Hz, 2 H) 3.28 (br. s., 4 H) 2.46 (t, J=6.0 Hz, 2 H) 2.34 (t, J=5.2 Hz, 4 H) 1.39 (s, 9 H) 1.09 (t, J=7.0 Hz, 3 H). MS (ESI+) m/z 259 [M+H]+ .

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 592-55-2.

Reference:
Patent; KANCERA AB; MELLSTEDT, Hakan; BYSTROeM, Styrbjoern; VAGBERG, Jan; OLSSON, Elisabeth; (302 pag.)WO2018/11138; (2018); A1;,
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Synthetic Route of 22236-10-8, A common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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 p-toluenesulfonic acid monohydrate (9.25 g, 48.6 mmol) in acetonitrile (65 mL)4- (difluoromethyloxy) aniline (2.00 mL, 16.2 mmol) was added at room temperature.To the reaction solution was added dropwise a solution of sodium nitrite (2.24 g, 32.4 mmol) and potassium iodide (6.72 g, 40.5 mmol) in water (11 mL) at 10 C., and the mixture was stirred at room temperature for 3 hours did.Water was added to the reaction solution,And extracted with ethyl acetate.The combined organic layers were successively washed with a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained crude product was purified by column chromatography (hexane) to obtain a pale pink oil (3.98 g, yield: 91%) of 1-difluoromethyloxy-4-iodobenzene.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; HOKKO CHEMICAL INDUSTRY COMPANY LIMITED; HANDA, MASAMI; MIZUTA, SATOSHI; HIRAI, KENJI; OKAMURA, DAIGO; GUSHIKAWA, TORU; (111 pag.)JP2015/848; (2015); A;,
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Reference of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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 flask is charged with bromoaryl derivative (1 eq.), piperazine (4-6 eq.), BINAP (0.06-0.22 eq.), NaOtBu (1.4-2.5 eq.) and toluene. The reaction mixture is degassed with N2 and Pd2(dba)3 (0.03-0.11 eq.) is added. Reaction mixture is heated at 100-110C for 2h-20h. The reaction mixture is extracted with HCl 1N solution. The aqueous layer is basified with NaOH 2N solution and extracted with EtOAc or DCM. The combined organic layers are washed with water and brine, dried (over anhydrous Na2SO4 or MgSO4), filtered and concentrated in vacuo to afford the expected arylpiperazine 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 1-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; DE CEUNINCK, Frederic, Andre; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (180 pag.)WO2017/211666; (2017); A1;,
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Synthetic Route of 25245-34-5, 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. 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

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.

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

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
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Electric Literature of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The synthetic route of 3,5-Dimethoxyphenylacetylene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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