Month: December 2020

Related Products of 89521-55-1, These common heterocyclic compound, 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, 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-(benzyloxy)benzene-1,2-diamine 4g (4.67 mmol) in xylenes (10 mL), 2-(4-hydroxyphenyl) acetic acid (9.34 mmol) and boric acid (0.46 mmol) were added. The resulting solution was refluxed for 48 h. After cooling to room temperature, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic phase was washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The residue was purified by flash silica gel (230-400 mesh) column chromatography to afford the title compounds 6g. Yield 22%; White solid; mp 105-109 C; IR (neat) 3400-2600 (br., peak), 2921, 2850, 1594, 1515, 1442, 1245, 1172,1098, 1022, 837, 784, 732; 1H NMR (300 MHz, Methanol-d4) delta 7.46-7.57 (m, 2H), 7.26-7.40 (m, 3H), 7.06-7.14 (m,4H), 6.75-6.80 (m, 1H), 6.68-6.74 (m, 2H), 5.23 (s, 2H),4.08 (s, 2H); 13C NMR (100 MHz, Methanol-d4) delta 157.7,155.3, 149.1, 138.9, 131.0, 129.7, 129.4, 129.2, 129.1,124.1, 116.8, 116.7, 108.8, 105.7, 71.6, 35.2; HRMS (ESI) Calcd for C21H18N2O2 [M + H]+ 331.1446, found 331.1471.

The synthetic route of 89521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boggu, Pulla Reddy; Venkateswararao, Eeda; Manickam, Manoj; Kim, Youngsoo; Jung, Sang-Hun; Archives of Pharmacal Research; vol. 40; 4; (2017); p. 469 – 479;,
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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. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Bromo-1-methoxy-2-methylbenzene

4-[1-(3-Bromo-phenyl)-vinyl]-1-methoxy-2-methyl-benzene Tetrahydrofuran (5 mL) was added to magnesium turnings (330 mg, 13.56 mmol) in a dried apparatus consisting of 250 mL 3-necked flask, addition funnel and reflux condenser. Then 5 mL of a solution of 4-bromo-2-methylanisole (2.5 g, 12.43 mmol) in tetrahydrofuran (15 mL) was added, followed by a drop of bromine. The exothermic reaction started instantaneously, and the 4-bromo-2-methylanisole solution was added at such a rate to maintain gentle reflux of the reaction mixture (25 min). After complete addition, the light-brown hazy Grignard solution was stirred for another 2 h at 40 C. The mixture was then cooled to 0 C. and a solution of 3-bromoacetophenone (1.42 mL, 11.3 mmol) in tetrahydrofuran (15 mL) was added dropwise over 30 min. After the addition was complete, the mixture was stirred overnight, followed by cooling in an ice bath and careful quenching with 0.5 N cold HCl. After further dilution with ethyl acetate (100 mL) and water (100 mL), the layers were separated and the aqueous layer extracted once more with ethyl acetate (50 mL). The organic layer was dried (magnesium sulfate), filtered and evaporated under reduced pressure. The residual material (tertiary alcohol) was dissolved in a mixture of acetic acid/sulfuric acid (4 mL of acetic acid, 0.12 mL of sulfuric acid) and the reaction mixture was stirred for 3 h at room temperature; then it was examined by LC-MS which showed the complete formation of desired product. The solution was quenched with ice and dichloromethane (20 mL) was added. The two phases formed and were separated. The organic layer was washed with a saturated solution of sodium bicarbonate and brine. It was then dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Crude was purified by flash chromatography eluding with cyclohexane. 1.9 g of desired product was obtained as colorless oil (Yield: 55%). Mass (calculated) C16H15BrO [303] M-H+ not observed LC Rt=3.05 min (5 min method) 1H-NMR (CDCl3): 2.23 (s, 3H); 3.86 (s, 3H); 5.35 (s, 1H); 5.43 (s, 1H); 6.80 (m, 1H); 7.13 (m, 2H); 7.21 (m, 1H); 7.28 (m, 1H); 7.46 (m, 1H); 7.53 (m, 1H)

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
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Related Products of 36449-75-9, 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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 25-mL round-bottom flask, were introduced compound 4.7 (450 mg, 1.25 mmol, 1.00 equiv), l-(2-bromoethyl)-2-methoxybenzene (400 mg, 1.86 mmol, 1.50 equiv), N,N-dimethylformamide (4 mL) and K2CO3 (260 mg, 1.87 mmol, 1.50 equiv). Reaction was stirred for 10 h at 80C and then quenched by the addition of 5 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The crude was purified by re-crystallization from ethyl ether to provide 450 mg (73%) of compound 4.8 as an off-white solid.

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

Reference:
Patent; NIMBUS APOLLO, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; BORG, George; MASSE, Craig E.; WO2014/182943; (2014); A1;,
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Electric Literature of 16452-01-0, The chemical industry reduces the impact on the environment during synthesis 16452-01-0, name is 3-Methoxy-4-methylaniline, I believe this compound will play a more active role in future production and life.

g. 2-bromo-5-methoxy-4-methyl-aniline. To a solution of 3-methoxy-4-methyl-aniline (8.19 g, 59.71 mmol) in dichloromethane (200 mL), was added tetrabutylammonium tribromide (28.79 g, 59.71 mmol) and the reaction mixture was stirred at room temperature for 2.5 hrs. Aqueous NaHCO3 was added and the layers separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 11.05 g of 2-bromo-5-methoxy-4-methyl-aniline (85% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.75 (s, 3 H), 3.95 (br s, 1 H), 6.27 (s, 1 H), 7.13 (s, 1 H).

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, 3-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfahl, Magnus; Tachdjian, Catherine; Spruce, Lyle W.; Al-Shamma, Hussien A.; Boudjelal, Mohamed; Fanjul, Andrea N.; Wiemann, Torsten R.; Pleynet, David P.M.; US2003/144329; (2003); 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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-(2-Bromoethoxy)-4-fluorobenzene

EXAMPLE 113 4-(3-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride STR149 From a mixture of 4-(3-fluorobenzyl)piperidine hydrochloride (500 mg, 2.18 mmol), 2-(4-fluorophenoxy)ethyl bromide (501 mg, 2.29 mmol) and K2 CO3 (615 mg, 4.45 mmol) in CH3 CN (20 mL) was obtained the title compound as a fluffy, colorless, crystalline solid (360 mg, 81%): mp 155-157 C., 1 H NMR (CDCl3) 1.65-1.90 (m, 3H), 1.98-2.16 (m, 2H), 2.62 (d, J=7.2 Hz, 2H), 2.65-2.85 (m, 2H), 3.20-3.53 (m, 2H), 3.67 (d, J=12 Hz, 2H), 4.51 (t, J=4.5 Hz, 2H), 6.78-7.10 (m, 7H), 7.19-2.28 (m, 1H), 12.64 (bs, 1H); Anal. Calcd for C20 H24 ClF2 NO: C, 65.30; H, 6.58; N, 3.81. Found: C, 65.35; H, 6.58; N, 3.77.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); A;,
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Application of 261762-35-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 261762-35-0 name is 5-Bromo-1,2-difluoro-3-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 20 N-( 1 -(7-chloro-4,5 -difluoro- 1 -hydroxy- 1 ,3-dihydrobenzo[cl [ 1 ,2″|oxaborol-6-yloxy”)-2-cva nopropan-2-yl)-4-(trifluoromethoxy)benzamide To a solution of 5-bromo-l,2-difluoro-3-methoxybenzene (8.9 g, 39.9 mmol) in THF (200 mL), LDA (17.6 mL, 43.9 mmol) is added dropwise at -78C and the mixture is stirred at the same temperature for 2 h. DMF (9.6 g, 131.7 mmol) is added at -78 C, and the mixture is stirred at -78C for 4 h. The reaction is quenched with saturated aq. NH4C1, extracted with EA, dried over Na2S04, and recrystallized to afford the desired product as a white solid (6 g, yield 60 %). :H NMR (400 MHz, CDC13): delta 10.20 (s, IH), 7.04-7.06 (m, 1H), 3.99 (s, 3H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-difluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; ANACOR PHARMACEUTICALS INC.; AKAMA, Tsutomu; JARNAGIN, Kurt; PLATTNER, Jacob J.; PULLEY, Shon Roland; WHITE, William Hunter; ZHANG, Yong-Kang; ZHOU, Yasheen; WO2014/149793; (2014); A1;,
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Synthetic Route of 171290-52-1, The chemical industry reduces the impact on the environment during synthesis 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, I believe this compound will play a more active role in future production and life.

(S) -3- (5-amino-3-bromo-4-cyano-1H -Pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7c (5g, 14.1mmol), cuprous iodide (0.6g, 2.8mmol), triethylamine (9mL), [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride (2g, 2.8mmol) And N, N-dimethylformamide (150mL) were heated to 80 C under the protection of argon, and 1-ethynyl-3,5-dimethoxybenzene (14g, 84.5mmol) was added in portions. And stir for 2 hours.After cooling to room temperature, the reaction solution was poured into water and extracted with ethyl acetate (200 mL ¡Á 3).The organic phases were combined, dried over anhydrous sodium sulfate, filtered to remove the drying agent, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 5/1) to obtain the target product (S) -3- ( 5-amino-4-cyano-3-((3,5-dimethoxyphenyl) ethynyl) -1H-pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7d (5 g, brown oil), yield: 81%.

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, 3,5-Dimethoxyphenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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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. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H7F3N2O

Step a. To a solution of 4-(trifluoromethoxy)benzene-l,2-diamine (CAS Number 658-89-9; 0.45 g, 2.34 mmol) in DMF (5 ml) was added urea (0.28 g, 4.66 mmol) at rt. The resulting reaction mixture was heated at 150C for 20 h. The reaction mixture was diluted with water (5 ml) and the brown precipitate was collected by vacuum filtration and dried under reduced pressure to yield 5- (trifluoromethoxy)-l,3-dihydro-2H-benzo[d]imidazol-2-one (0.28 g, 1.28 mmol). LCMS: Method C, 2.118 min, MS: ES+ 219.

The synthetic route of 658-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (88 pag.)WO2018/60742; (2018); A1;,
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Electric Literature of 707-07-3, 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 707-07-3 as follows.

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 101-55-3

4-Bromodiphenyl ether (X = Br) (3.74 g, 15 mmol) was dissolved in 1,4-dioxane (50 ml)Addition of pinacol diboronate(4.52 g, 18 mmol),Potassium acetate (1.78 g, 18 mmol).Then, the catalyst [1,1′-bis (diphenylPhosphine) ferrocene] palladium dichloride [Pd (dppf) 2Cl2] (1.5 mmol, 1.11 g).With stirring, heated to 100 C, the reaction 5h (TLCDetection of raw materials disappear).Then, Intermediate (14) (4.44 g, 10 mmol) was added, and the reaction was maintained at 100 C for 22 hours14 disappears).Then, after distilling off the organic solvent, Intermediate (9) (yellow solid, 3.41 g, yield 70%, chemical purity and optical purity> = 99%) was obtained.

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anrun Pharmaceutical (Suzhou) Co., Ltd.; Hong Jian; Liu Guobin; (12 pag.)CN104557945; (2017); B;,
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