Tag: M.W=200-300

Electric Literature of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Under an argon atmosphere, NaH (4.11 g, 103 mmol, 60% purity) was added to a solution of ethyl 2-(4-bromophenyl)acetate (10 g, 41.1 mmol) in anhydrous DMF (200 mL) at 0C. The resulting mixture was stirred at 0C for 0.5 h. l-bromo-2-(2-bromoethoxy)ethane (9.5 g, 41.1 mmol) was added and then stirred at 0C for 1 h. NaH (4.11 g, 103 mmol, 60% purity) was added, and the reaction stirred at 0C for an additional 1 h. The resulting mixture was poured into saturated aqueous NH4Cl (200 mL) and extracted with ethyl acetate (3 x50 mL). The combined organic layers were washed with water (2 x50 mL), brine (50 mL), dried over Na2S04, filtered (1369) concentrated, and then purified by column chromatography (Si02, petroleum ether: ethyl (1370) acetate=5 : l) to give ethyl 4-(4-bromophenyl)tetrahydro-2//-pyran-4-carboxylate (5 2 g? 40%) as a yellow oil. 1H MR (400 MHz, CDCI3): d 7.43 (d, 2H), 7.22 (d, 2H), 4.17 (q, 2H), 3.95 (t, 2H), (1371) 3.58 (t, 2H), 2.52 (d, 2H), 1.96 (t, 2H), 1.21 (t, 3H); LCMS: 312.9 [M+H]+.

Statistics shows that 1-Bromo-2-(2-bromoethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 5414-19-7.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; HUDSON, Andrew R.; CHEN, Mi; NAGASAWA, Johnny Y.; (265 pag.)WO2019/241751; (2019); 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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H14ClNO

Example 52-1 NL- (4-benzyloxyphenyl)-4-methoxybenzamidine To a solutionof 4-benzyloxyaniline hydrochloride (3g) in tetrahydrofuran (15ML), 1.OM sodium bis (trimethylsilyl) amide in tetrahydrofuran (26. 7ML) wasadded dropwise at room temperature. After the mixture was stirred for20min, anisonitrile (1.69g) was added.The reaction mixture was stirred for 4hrs, and then poured into 300ML OFice-water. The precipitates were collected by filtration, washed withdiisopropyl ether to give the target compound (3.3g).1H NMR (200MHZ, DMSO-D6, D) : 3.8 (3H, s), 5.05 (2H, s), 6.09 (2H, bs),6.74-6. 8 (2H, m), 6.96 (4H, d, J=8.5Hz), 7.29-7. 49 (5H, m), 7.92 (2H,d, J=8.9Hz).MS m/e: 333 (M+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; FUJISAWA PHARMACEUTICAL CO., LTD.; WO2004/99130; (2004); A2;,
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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 450-88-4 as follows. Quality Control of 1-Bromo-4-fluoro-2-methoxybenzene

General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2¡Á10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 1-Bromo-4-fluoro-2-methoxybenzene was borylated using the general procedure described above. After workup, a white solid was obtained (0.313 g, 95%): mp 104-105 C.; 1H NMR (500 MHz, CDCl3) delta 7.89 (d, J=6.5 Hz, 1H), 6.61 (d, J=11.0 Hz, 1H), 3.72 (s, 3H), 1.35 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 167.6 (d, J=251.2 Hz), 159.5 (d, J=11.4 Hz), 140.2 (d, J=10.4 Hz), 108.3 (d, J=22.7 Hz), 105.9 (d, J=2.9 Hz), 83.9, 56.4, 24.8; 19F NMR (470 MHz, CDCl3) delta 100.4; 1113 NMR (160 MHz, CDCl3) delta 29.5 (br s).

According to the analysis of related databases, 450-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); 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. HPLC of Formula: C8H9BrO

Upon stirring a solution of p-anisoyl chloride (8.53 g, 50 mmol) and beta-bromophenetole (10.05 g, 50 mmol) in 20 mL of anhydrous nitrobenzene at 5 C. under a nitrogen atmosphere, 7.33 g (55 mmol) of anhydrous aluminum chloride was added portionwise. The resulting mixture was stirred at room temperature for 1 hour then at a reduced pressure for 5 minutes to remove the HCl gas produced during the reaction. Stirring was continued at room temperature under the nitrogen atmosphere for another hour. Nitrobenzene was removed at 45 C./0.4 mmHg and the solids deposited were dissolved in 60 mL of chloroform. Upon stirring the solution in an ice bath, 25 mL of 2M HCl was added portionwise. The organic layer was separated and washed with 20 mL of saturated sodium hydrogencarbonate aqueous solution, dried over solid NaHCO3, and filtered through a filter paper. Solvent was removed from the filtrate using a rotary evaporator and the crude product was purified by silica gel column chromatography (particle size 32-63) in CHCl3. The product with Rf=0.26 was collected and recrystallized from chloroform/hexane to give 14.44 g (43 mmol, 86% yield) of white flakes. m.p. 112.2-113.3 C. E.A. C16H15BrO3, calculated C 57.32, H 4.52, Br 23.83; found C 57.40, H 4.55, Br 23.76. 1H-NMR (DMSO-d6) delta 3.86 (m, 5H, -OCH3, -OCH2CH2Br), 4.44 (t, 2H, J=5.40, 5.04 Hz, -OCH2CH2Br), 7.08 (d, 2H, J=8.64 Hz, aromatic H’s), 7.11 (d, 2H, J=8.64 Hz, aromatic H’s), 7.71 (d, 2H, J=2.52 Hz, aromatic H’s), 7.73 (d, 2H, J=2.52 Hz, aromatic H’s). 13C-NMR (DMSO-d6) 31.17, 55.51, 67.97, 113.75, 114.33, 129.88, 130.44, 131.84, 161.11, 162.54, 193.12.

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

Reference:
Patent; Mills, Randell L.; Wu, Guo-Zhang; US2005/80260; (2005); A1;,
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Related Products of 5473-01-8,Some common heterocyclic compound, 5473-01-8, name is 2-Bromo-6-methoxyaniline, molecular formula is C7H8BrNO, 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 solution of 2-bromo-6-methoxyaniline (1.539 g, 7.62 mmol) in tetrahydrofuran (12 mL) was added 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.297 g, 0.364 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.35 M in tetrahydrofuran solution of cyclobutylzinc(II) bromide (40 mL, 14.00 mmol) was added dropwise over 5 minutes. The reaction was stirred for 15 hours at ambient temperature. Additional cyclobutylzincbromide solution (24 mL) was added and the mixture was stirred at ambient temperature for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (50 mL), diluted with methyl tert-butyl ether (400 mL), and the layers were separated. The organic layer was concentrated in vacuo to give crude material that was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-60percent methyl tert-butyl ether/hexanes over 40 minutes to provide the title compound. 1H NMR (501 MHz, chloroform-d) delta ppm 6.81 (ddd, J=7.5, 1.7, 0.8 Hz, 1H), 6.77 (t, J=7.7 Hz, 1H), 6.74 (dd, J=7.9, 1.8 Hz, 1H), 3.88 (s, 3H), 3.75 (d, J=17.6 Hz, 2H), 3.59-3.49 (m, 1H), 2.47-2.37 (m, 2H), 2.27-2.16 (m, 2H), 2.09 (tdt, J=10.5, 9.3, 7.9 Hz, 1H), 1.95-1.86 (m, 1H)+ MS (ESI+) m/z 178 (M+H)+.

The synthetic route of 5473-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); 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. 4698-11-7, name is 10-Methoxy-5H-dibenzo[b,f]azepine, A new synthetic method of this compound is introduced below., SDS of cas: 4698-11-7

Example 1 Step 1. Preparation of 10-Methoxy-5H-dibenz [b, f] azepine-5-carbonyl chloride 100 gms of 10 Methoxy iminostilbene is dissolved in 300 mi chloroform & cooled to 0 C Bis (trichlor methyl) carbonate (BTC) 65 gms is added. 67 gms of triethyl amine (TEA) in 100 ml chloroform is added slowly over a period of6 hour & maintaining the temperature 0-5C. Temperature is then increased to 25-30 C 1& maintained for 8 hour. The reaction mixture is poured into 300 mi water & layers are separated. Chloroform is evaporated 10-Methoxy-5H-dibenz [b, f] azepine-5-carbonyl chloride is isolated in methanol. Yield obtained is 110 gms (86%) of theoretical.Example 3 Step 1. Preparation of 10-Methoxy-5H-dibenz [b, f] azepine-5-carbonyl chloride 100 gms of 10-Methoxy iminostilbene is dissolved in 300 ml chloroform & cooled to 0C and 45 gms Bis (trichlor methyl) carbonate (BTC) is added followed by he addition of 45 gms-of-TEA in 100 ml chloroform over a period-of 8 hours maintaining the temperature at 0-5C. The temperature is then increased to 25-30C & maintained for 2 hours. The reaction mixture is poured into 300 ml water layers are separated. Chloroform is evaporated & product is isolated in methanol. Yield obtained is 100 gms (80% of theoretical).

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; AMOLI ORGANICS LTD.; WO2005/66133; (2005); A2;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., name: ((3-Bromopropoxy)methyl)benzene

[(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 (2x) and then acidified to pH 3 with conc. HCl. The aqueous layer was extracted with EtOAc (3x) 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.

According to the analysis of related databases, 54314-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shakespeare, William C.; Sawyer, Tomi K.; Metcalf III, Chester A.; Wang, Yihan; Bohacek, Regine; US2003/130234; (2003); A1;,
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Related Products of 4463-59-6, 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. 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a pre-cooled suspension of 2-bromo-5-fluorophenol (5 g, 26.18 mmol) and potassium carbonate (10.84 g, 78.54 mmol) in DMF (15 mL) at 0-5 C., was added methyl iodide (4.75 mL, 39.27 mmol) and the resulting reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (3*50 mL). The organic layers were combined, washed with saturated brine solution (20 mL) and dried over Na2SO4, filtered and concentrated in vacuo to afford 1-bromo-4-fluoro-2-methoxybenzene as a colourless liquid in 93% yield, 5.00 g. 1H NMR (400 MHz, DMSO-d6): delta ppm 3.86 (s, 3H), 6.74-6.79 (m, 1H), 7.06 (dd, 1H), 7.57-7.65 (m, 1H).

The synthetic route of 1-(2-Bromoethoxy)-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Limited; Omoto, Kiyoyuki; Owen, Robert McKenzie; Pryde, David Cameron; Watson, Christine Ann Louise; Takeuchi, Mifune; US2014/171435; (2014); A1;,
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Some common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, molecular formula is C8H8Br2O, 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. Computed Properties of C8H8Br2O

4-(4-Bromobenzoyl)piperidine (1.4 g, 5.3 mmol),1-(2-Bromoethoxy)-4-bromobenzene (1.9 g, 6.9 mmol), KI (1.6 g, 10 mmol) and 30 mL of ethanol were added to a 100 mL eggplant-shaped flask and heated under reflux, and 5 mL of a 20% KOH solution was added dropwise. The addition was completed in 10 minutes.Reflux for 24 hours, evaporate the solvent and dissolve in 30 mL of dichloromethane.The organic layer was washed three times with 20 mL of water, and the organic layer was concentrated.A mixture of ethyl acetate and petroleum ether was used as the eluent.Column chromatography gave 2.3 g of a white solid with a yield of 92.0%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18800-30-1, its application will become more common.

Reference:
Patent; Southeast University; Zhong Yan; Fang Tiantian; Chen Liyi; (24 pag.)CN110437136; (2019); 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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 103291-07-2

In a 1 I three necked round bottom flask, flame dried, under argon, 2-fluoro-5-bromoanisole (27.40 g; 133.64 mmol; 1.20 eq.) was diluted in THF (200 mL) and the mixture was cooled to -78C. Then, n-Butyllithium 1.6M in hexane (98.0 mL; 1.6 mol/L; 156.8 mmol; 1.41 eq.) was slowly added during 20 min, keeping temperature below -65C and the reaction was stirred at -78C for 1h. Next, a solution of 4-chloro-N-methoxy-N-methyl-pentanamide (20.00 g; 111.33 mmol; 1.00 eq.) in THF (100 mL) was slowly added to the lithiated species during 25 min, keeping temperature below -65C. The reaction was then stirred 40 min at -78C and quenched by addition of aqueous 1N HCI (500 mL). The mixture was allowed to warm to rt and was extracted EtOAc (3 x 250 mL). Combined organic layer was dried over MgS04, filtered, and concentrated to dryness to give 4-chloro-1-(4-fluoro-3-methoxy-phenyl)pentan-1-one (32.50 g; quantitative ; 47% LC/MS purity) as a yellow liquid, used in the next step without further purification.

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 103291-07-2.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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