Month: December 2020

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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6770-38-3, The chemical industry reduces the impact on the environment during synthesis 6770-38-3, name is 1,4-Bis(methoxymethyl)benzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 19 The procedure of Example 9 was repeated, except that 1 mmol of 1,4-bis(methoxymethyl)benzene was used instead of 4-methoxymethyltoluene to give terephthalaldehyde (yield: 53%) and 4-methoxymethylbenzaldehyde (yield: 20%) at a conversion rate from 1,4-bis(methoxymethyl)benzene of 96%.

The chemical industry reduces the impact on the environment during synthesis 1,4-Bis(methoxymethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daicel Chemical Industries, Ltd.; US6201156; (2001); B1;,
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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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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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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. 4179-19-5, name is 3,5-Dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows., 4179-19-5

231.6 g (1.5 mol) of 3,5-dimethoxytoluene are dissolved in 1 litre of diethylether, followed by dropwise addition, under nitrogen and at room temperature, of 1 litre of a 1.6 N solution of butyllithium (1.6 mol) in hexane. The reaction mixture is left for 18 hours at room temperature and then, after cooling to 30 C., 1 litre of diethylether is added and carbon dioxide is bubbled through for one hour, while maintaining the temperature at 30 C. The reaction mixture is taken up in 6 litres of 2 M sodium hydroxide solution, the aqueous phase is separated out after settling has taken place and is acidied with 6 N hydrochloric acid solution. The precipitate formed is ltered off, rinsed with water and dried under vacuum at 40 C. in order to obtain white crystals; m.p.=187 C.; yield=88%.

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; Bignon, Eric; Bras, Jean Pierre; De Cointet, Paul; Despeyroux, Pierre; Frehel, Daniel; Gully, Danielle; US2004/43995; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 458-03-7, name is 1-Ethoxy-3-fluorobenzene, 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 458-03-7, 458-03-7

First Step In a reaction vessel under a nitrogen atmosphere, 1.94 g (7.2 mmol) of 2-(4-ethoxy-2-fluoro-3-trimethylsilylphenyl)acetate (No. 5) obtained in the fourth step in Example 1 was dissolved into 25 mL of THF. The solution was cooled to 0 C., 8.6 mL (14.4 mmol) of s-butyllithium (1.67 M n-hexane solution) was added dropwise thereto, and subsequently the reaction mixture was heated to room temperature and stirred for 30 minutes. Subsequently, the resultant reaction mixture was cooled to -70 C., a THF (15 mL) solution of 1.9 g (7.2 mmol) of 2-(trans-4-propyl-cyclohexyl)cyclohexyl-oxetane (No. 26) obtained according to a method described in JP 2000-8040 A, and subsequently a THF (3 mL) solution of 1.08 mL (8.6 mmol) of boron trifluoride-diethyl ether complex were added dropwise thereto.

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, 1-Ethoxy-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JNC CORPORATION; JNC PETROCHEMICAL CORPORATION; Goto, Mayumi; Fujimori, Sayaka; US9102871; (2015); B2;,
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702-24-9, 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. 702-24-9 name is 4-Methoxy-N-methylbenzylamine, 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.

3-( 5-amino-4-fluoro-2-methylphenyl)-7 -chloro-1-methyl-1 ,6-naphthyridin-2(1H)one(1.36 g, 4.28 mmol, 1.00 eq), 4-methoxy-N-methylbenzylamine (0.971 g, 6.42 mmol,1.50 eq) and DBU (0.960 mL, 6.42 mmol, 1.50 eq) were combined in NMP (20 mL) andheated at 180¡ãC under Ar overnight. The mixture was cooled to R T and poured onto H20(200 mL). The resulting solids were collected by filtration, rinsed very well with H20, driedon the filter to dampness and then dissolved in EtOAc. The solution was dried (MgS04),filtered and evaporated to afford 7-(( 4-methoxybenzyl)(methyl)amino )-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (1.86 g, 100percent yield) as a brittlebrown foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): 88.45 (s, 1H), 7.63 (s, 1H), 7.16 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 8.8 Hz, 2H), 6.86-6.82 (m,1H), 6.57 (d, J = 9.6 Hz, 1H), 6.29 (s, 1H), 4.88 (br s, 2H), 4.85 (s, 2H), 3.69 (s, 3H), 3.52 (s,3H), 3.07 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 433.3 [M+H(

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

Reference:
Patent; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2013/184119; (2013); 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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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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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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