Tag: M.W=200-300

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. 52411-34-4, name is 1,2-Bis(o-aminophenoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., 52411-34-4

Then, triphenylphosphine dibromide (0.11 mol) and 150 ml of 1,2-dichloroethane were fed to a reactor equipped with a stirrer, a heater and a dropping funnel in an N2 atmosphere and stirred. A solution obtained by dissolving the intermediate product B (0.05 mol) and triethylamine (0.25 mol) in 50 ml of 1,2-dichloroethane was gradually added dropwise to the resulting mixture at 25 C. After the end of addition, a reaction was carried out at 70 C. for 5 hours. Thereafter, the reaction solution was filtered, and the filtrate was separated with 100 ml of water 5 times. An organic layer was dehydrated with 5 g of sodium sulfate and 1,2-dichloroethane was removed under reduced pressure to obtain an intermediate product C (triphenylphosphine derivative).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; TEIJIN LIMITED; Matsuno, Yuichi; Mitsunaga, Masaki; Oda, Jitsuo; Furuki, Masatsugu; Shoji, Shinichiro; Kitamura, Takuro; Shibata, Yoshitaka; (51 pag.)US9650350; (2017); B2;,
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101-55-3, 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. 101-55-3, name is 1-Bromo-4-phenoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4B. Alternative Preparation of (5) where R 5 is 4-(4-Bromophenoxy)phenyl A solution of 4-bromodiphenyl ether (50 g, 200.7 mmol) in methylene chloride (118 ml) was cooled to 0C and chlorosulfonic acid (14.7 ml, 220.8 mmol) was added dropwise over a 20 minute period. The solution was stirred an additional 10 minutes, warmed to room temperature and stirred an additional 1 hour. To this mixture was added oxalyl chloride (23.6 ml, 270.9 mmol), followed by N,N-dimethylformamide (1.5 ml) as a catalyst, and the mixture refluxed for 2 hours. The mixture was cooled to room temperature, and additional oxalyl chloride (23.6 ml, 270.9 mmol) was added, the mixture refluxed for 3 hours, cooled to room temperature and stirred 12 hours more. The solution was concentrated to an oil, azeotroped several times using methylene chloride and put under high vacuum (1 torr) for several hours until the mixture had completely solidified. This mixture was immediately dissolved in methylene chloride (160 ml) which was added dropwise to a solution of triphenylphosphine (157.0 g, 602 mmol) in methylene chloride (160 ml) containing N,N-dimethylformamide (4 ml, 52.2 mmol). The mixture was stirred 2 hours, diluted with 1M aqueous hydrochloric acid (300 ml) and stirred for 1 hour. The aqueous layer was separated, extracted with methylene chloride (200 ml), and the organic layers were combined, washed with 200 ml of brine, dried (MgSO4) and concentrated in vacuo.The resulting solid was further purified through trituration with 750 ml of hexane. The solid was then dissolved in 750 ml of diethyl ether, extracted with 2M aqueous sodium hydroxide (2 x 350 ml), and the basic aqueous layer back extracted using diethyl ether (2 x 400 ml). The aqueous layer was adjusted to pH 2, extracted with diethyl ether (3 x 200 ml) and the combined organic layers dried (MgSO4) and concentrated to afford 4-(4-bromophenoxy)thiophenol (45.6 g, 81%). 1H-NMR (CDCl3) delta 3.43 (s, 1H), 6.86 (d, J= 8.9 Hz, 2H), 6.89 (d, J= 8.6 Hz, 2H), 7.28 (d, J= 8.6 Hz, 2H), 7.43 (d, J= 8.9 Hz, 2H).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AGOURON PHARMACEUTICALS, INC.; EP780386; (1997); A1;,
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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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., 22094-18-4

To a solution of 2-(2,5-difluoro-4-methylphenyl)acetonitrile (16.7 g, 100 mmol) in DMSO (200 mL) was added NaH (8 g, 200 mmol, 60% oil dispersion), portion-wise, at RT. The reaction was stirred for 1 h at RT, and then l,3-dibromo-2,2-dimethoxypropane (39.3 g, 150 mmol) was added. The mixture was heated at 60 C for 6 h. The reaction was quenched with water (100 mL) at 0 C and extracted with EtOAc (2 x 100 mL). The organic extracts were combined and washed with brine (2 x 50 mL), dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleumn ether/EtOAc (4/1) as eluting solvents to afford the title compound as a yellow solid (12 g, 45% yield). lU NMR(400 MHz, DMSO- ) delta 7.36-7.28(m, 2H), 3.18(s, 3H), 3.05(s, 3H), 3.03 (d, / = 13.6 Hz, 2H), 2.77 (d, / = 13.6 Hz, 2H), 2.24 (d, / = 1.6 Hz, 3H). LCMS (ESI): m/z = 268.0 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; GANCIA, Emanuela; LADDUWAHETTY, Tammy; VESEY, David; WINSHIP, Paul; RENE, Olivier; (168 pag.)WO2017/5900; (2017); A1;,
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22094-18-4, 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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of NaH (4.08 g, 102 mmol) (60% in oil) in DMF (50 mL) was added a solution of 2-(4-bromophenyl)acetonitrile (10 g, 51 mmol) in DMF (50 mL) dropwise at 0 C, followed by the addition of 1,3 -dibromo-2,2-dimethoxy propane (13.4 g, 51.0 mmol) at 0 C. The mixture was stirred at 60 C for 18 h. After cooling to RT, the reaction was quenched by adding water (250 mL) and extracted with EtOAc (150 mLx3). The organic layers were combined, washed with brine, dried over Na2SC>4, filtered and concentrated in vacuo to afford a residue, which was purified by column chromatography on silica gel (PE : ethyl acetate =40: 1 to 30: 1) to give the title compound. MS (EI) m/z 296 [M+H]+.

The synthetic route of 22094-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); A1;,
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101-55-3, Adding some certain compound to certain chemical reactions, such as: 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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 101-55-3.

General procedure: Reactions were conducted using standard dry box techniques and all solvents were distilled over Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.sodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was then purified by column chromatography on silica gel.

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 101-55-3.

Reference:
Article; Semmes, Jeffrey G.; Bevans, Stephanie L.; Mullins, C. Haddon; Shaughnessy, Kevin H.; Tetrahedron Letters; vol. 56; 23; (2015); p. 3447 – 3450;,
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74137-36-3, These common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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.

Succinic acid mono-{3-[4-chloro-3-(3,5-dicyano-phenoxy)-2-fluoro-benzyl]-4-methyl-5-oxo-4,5-dihydro-[1,2,4]triazol-1-ylmethyl} ester was prepared in a similar manner except steps 1 and 2 were omitted and 3,5-dibromophenol was used in the place of 3-bromo-5-chlorophenol in step 3 to afford I-4: mp 141.6-143.3¡ã C., MS (ES-): m/z 512, 1H NMR (d6-DMSO, 300 MHz) delta 12.2 (br.s, 1H), 8.23 (t, J=1.2 Hz, 1H), 7.95 (d, J=1.2 Hz, 2H), 7.52 (dd, J=1.5, 8.6 Hz, 1H), 7.35 (t, J=7.8 Hz, 1H), 7.34 (t, J=7.8 Hz, 1H), 5.63 (s, 2H), 4.09 (s, 2H), 3.14 (s, 3H) 2.52-2.43 (m, 4H). Anal. Calcd for C23H17FClN5O6: C, 53.76; H, 3.33; N, 13.63. Found: C, 53.68; H, 3.47; N, 13.35. 3,5-Dibromophenol was prepared from 3,5-dibromoanisole by demethylation with HBr/HOAc.

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 74137-36-3.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
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19056-41-8, The chemical industry reduces the impact on the environment during synthesis 19056-41-8, name is 3-Bromo-4-methoxyaniline, I believe this compound will play a more active role in future production and life.

A flask containing compound QQ (0.966 g, 1.48 mmol), 4-amino-2-bromoanisole (0.35 g, 1.78 mmol), tris(dibenzylidineacetone)dipalladium(0) (0.068 g, 0.074 mmol), BINAP (0.092 g, 0.148 mmol), and sodium tert-butoxide (0.569 g, 5.92 mmol) was flushed with nitrogen, and then anhydrous o-xylene (30 mL) was added. The mixture was heated at 115 C. in an oil bath for two hours. At this time, the reaction was cooled to room temperature and the solvent was removed under reduced pressure. The brownish residue was redissolved in dichloromethane and filtered through a bed of celite. The filtrate was concentrated to dryness under reduced pressure, dissolved in THF (20 mL) and purged with nitrogen. Tetrabutylammonium fluoride (1.0 N in THF, 4.5 mL, 4.5 mmol) was added and the solution was stirred for 18 hours at room temperature. The solvent was removed under reduced pressure, and the residue partitioned between water and DCM. The organic layer was washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (1-10% MeOH in DCM) to give compound RR.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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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. 21702-84-1 name is 2,4-Dibromo-1-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. 21702-84-1

General procedure: A Teflon-lined autoclave (25 mL) was charged with MeONa (1.08 g, 20.0 mmol), MeOH (10 mL), CuCl (40 mg, 0.40 mmol), HCOOMe (0.25 mL, 0.97 g/mL, 4.0 mmol), and monohaloarene (10.0 mmol) then heated to 115 C, with stirring, for 2 h. After completion of the reaction, the reactor was cooled to room temperature. The mixture was stirred for 0.5 h in the open, then concentrated to recover pure MeOH. Diethyl ether (15 mL) and dilute hydrochloric acid (1.6 M, 15 mL) were added to the residue. The mixture separated into two layers, and the aqueous phase was extracted with diethyl ether (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography on silica gel (mobile phase: petroleum ether-ethyl acetate 15:1) to furnish 1 (conversion and selectivity were determined by GC-MS analysis). The purity of the recovered MeOH was measured as more than 99 % by GC, and the water content of the recovered MeOH was measured as less than 0.12 % by use of the Karl Fischer method.

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

Reference:
Article; Guo, Ying; Ji, Si-Zhe; Chen, Cheng; Liu, Hong-Wei; Zhao, Jian-Hong; Zheng, Yu-Lin; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 41; 11; (2015); p. 8651 – 8664;,
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1462-37-9, name is ((2-Bromoethoxy)methyl)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. 1462-37-9

After flushing the interior of the vessel with nitrogen, under nitrogen, 8.41 g (210 mmol) of sodium hydride (oily) and 80 ml of dry tetrahydrofuran were added to a 1000 ml four-necked flask, and while cooling with an ice-water bath, 34.00 g (100 mmol) in 350 ml of tetrahydrofuran was added dropwise. Immediately after the dropwise addition of DCMI in tetrahydrofuran solution, bubbles that appeared to be H 2 were observed. After foaming subsided, the temperature was raised to room temperature and stirred for 1 hour. Thereafter, while cooling the flask again with an ice-water bath, a solution of 50.01 g (233 mmol) of benzyl-2-bromoethyl ether dissolved in 50 ml of dry THF was added dropwise. After the dropwise addition, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes, then heated to 60 to 70 ¡ã C. and stirred for 18 hours. On the way, heating was stopped when benzyl-2-bromoethyl ether became a trace amount and consumption ceased almost at a time-dependent change by TLC.As a post-treatment, the flask was cooled with ice with stirring under nitrogen, 150 ml of ethyl acetate was added to the flask, then 100 ml of water was slowly added dropwise, the aqueous phase was separated off and the organic phase was washed with 100 ml of water For 2 times. The organic phase was concentrated with an evaporator to obtain 68.10 g of a viscous liquid with a yellowish tinge. Thereafter, silica gel column purification was carried out using a mixed solvent of hexane and ethyl acetate (hexane / ethyl acetate = 10/1 to 1/1 (volume ratio)), and the solvent was distilled off under reduced pressure to give the following compound 6 46.36 g (76.2 mmol: yield 76.2percent) was obtained as a viscous liquid.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; Machine: Mitsubishi ChemicalsCo ., Ltd .; Imai Nao Akira; Saito Yasuyo; Kawakami Kotoku; Fuji Tsuu Akira; (94 pag.)JP2017/222625; (2017); A;,
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446-59-3, A common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, molecular formula is C7H6BrFO, 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.

General procedure: The 2-bromo-1-ethoxy-4-fluoro-benzene (0.1 mol) was dissolved in THF (25 ml). The solution was cooled to -75 C and a solution of n-BuLi (9.73 ml, 2.4 M in hexane) was added slowly. The mixture was stirred for 30 min at -75 C. Trimethylborate (0.1 mol) was added within 5 min. Acetic acid (0.1 mol) and a 30% solution of H2O2 (0.1 mol) were added sequentially. The mixture was stirred for 30 min at 0 C and for 3 h at room temperature. Water was added and the mixture was extracted with ethyl acetate. The crude product was purified by column chromatography to yield the objected compound.

The synthetic route of 446-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Heng; Xu, Xiangqing; Chen, Yin; Qiu, Yinli; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen; European Journal of Medicinal Chemistry; vol. 89; (2015); p. 524 – 539;,
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