Analyzing the synthesis route of 101-55-3

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

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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The important role of 1,2-Bis(o-aminophenoxy)ethane

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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. 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).

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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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The origin of a common compound about 4-Bromo-3-methoxyaniline

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

19056-40-7, 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. 19056-40-7 name is 4-Bromo-3-methoxyaniline, 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.

A solution of BBr3 in dichloromethane (1.0 M, 12 mL,12 mmol) was added slowly to a solution of 4-bromo-3-methoxyaniline (800 mg, 3.96 mmol) in methylene chloride(15 mL) at 0C. The resulting brown solution was warmed toroom temperature and stirred for 24 h. After saturated aqueousNaHCO3 (30 mL) was added at 0C, the solution was extractedwith EtOAc (20 mL ¡Á 3). The combined organic layer wasdried with anhydrous Na2SO4, filtered and concentrated invacuum. The residue was purified by flash chromatographyover silica gel (petroleum-EtOAc = 2 : 1) to give 5-amino-2-bromophenol (665 mg, 88%). To a solution of 5-amino-2-bromophenol (55 mg, 0.29 mmol)and triethylamine (53 muL, 0.38 mmol) in tetrahydrofuran (THF)(3 mL) was added slowly benzoyl chloride (0.32 mmol) at 0C.The reaction mixture was then stirred at room temperature for30 min. After the reaction was quenched with water (10 mL),the solution was extracted with EtOAc (10 mL ¡Á 2). The combinedorganic layer was dried over anhydrous Na2SO4, filteredand concentrated in vacuum. The residue was purified bycolumn chromatography to afford the product 3 (74 mg, 87%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Liang, Jie; Tang, Yun-xiang; Tang, Xiang-zheng; Liang, Hua-ju; Gao, Yamin; Fang, Cuiting; Zhang, Tian-yu; Yan, Ming; Chemical and Pharmaceutical Bulletin; vol. 67; 4; (2019); p. 372 – 381;,
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The important role of 405-06-1

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 405-06-1.

405-06-1, Adding some certain compound to certain chemical reactions, such as: 405-06-1, name is 2-Fluoro-4-methoxy-1-methylbenzene, 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 405-06-1.

A 10 mL oven-dried Schlenk tube was charged with magnesium (57.6 mg, 2.4 mmol) and anhydrous THF (1.5 mL), 5 drops of diisobutylaluminium hydride (DIBAL) was added and stirred for 5 min to activate magnesium. 2-bromo-1,3,5-triisopropylbenzene (566 mg, 2 mmol) was added potion-by-potion with vigorous stirring. The tube was capped with a rubber septum and was heated to 70 C. for 2 h (A). In another 10 mL oven-dried Schlenk tube was charged with 2-fluoro-4-methoxy-1-methylbenzene (140 mg, 1 mmol) and anhydrous THF (3.5 mL). The tube was cooled to -78 C. and 1.6 M n-BuLi solution in hexane (0.64 mL, 1 mmol) was added dropwise over 10 min under vigorous stirring. The mixture was stirred at -78 C. for 40 min (B). A was transferred into to B by syringe over 15 min at -78 C. An additional 1 mL of THF was used to rinse the reaction and was also transferred to B. The combined reaction mixture was stirred at -78 C. for another 1 h and then slowly warmed to room temperature and vigorously stirred for overnight. At this time, the mixture was cooled to 0 C. using ice bath, and iodine (762 mg, 3 mmol) in 4 mL anhydrous THF was added drop-wise over 5 min, then the reaction mixture was stirred for 30 min, and then warmed to stir at room temperature for 2 h. Then, the mixture was quenched with saturated Na2S2O3 (aq.) solution until the red color of bromine disappeared. The aqueous phase was extracted with Et2O (10 mL¡Á3) and the combined organic phases were dried over anhydrous MgSO4. After concentration, the crude product was purified by silica gel chromatography (EtOAc/petroleum ether=1/20) followed by crystallization in methanol to get a white solid (185 mg, 34%), labeled as 2MeO-SMeTIP-I. 1H NMR (600 MHz, Chloroform-d) delta 7.46-7.29 (m, 4H), 7.25 (dd, J=8.3, 0.8 Hz, 2H), 7.12 (s, 1H), 6.78 (d, J=8.3 Hz, 1H), 3.97 (s, 3H), 2.73-2.59 (m, 1H), 2.54 (p, J=6.8 Hz, 1H), 2.37 (p, J=6.8 Hz, 1H), 2.13 (s, 3H), 1.37 (d, J=7.0 Hz, 3H), 1.28 (d, J=6.8 Hz, 3H), 1.18-1.07 (m, 6H), 0.88 (d, J=7.2 Hz, 3H), 0.82 (d, J=7.2 Hz, 3H) ppm. 13C NMR (151 MHz, Chloroform-d) delta 156.49, 147.77, 146.49, 144.69, 141.28 (d, J=23.7 Hz), 139.64, 138.22, 131.97, 131.47, 130.62, 130.17, 129.81, 127.88, 126.87 (d, J=11.2 Hz), 126.38, 120.38 (d, J=35.2 Hz), 109.03, 56.39, 34.27, 32.38, 30.78, 30.26, 29.50, 24.63 (d, J=5.6 Hz), 24.47, 24.29, 24.22, 24.11, 23.42 (d, J=11.7 Hz), 21.54 ppm.

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 405-06-1.

Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (2016); A1;,
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Discovery of 5111-65-9

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 2-Bromo-6-methoxynaphthalene.

Adding some certain compound to certain chemical reactions, such as: 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, 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 5111-65-9. 5111-65-9

After 2-bromo-6-methoxynaphthalene (200 mg, 0.844 mmol), sodium azide (110 mg, 1.69 mmol), proline (126 mg, 1.10 mmol), and copper(I) oxide (121 mg, 0.844 mmol) were added to degassed DMSO (1.7 ml), this mixture was heated at 100 C. for 11 hours. The reacted solution was cooled to room temperature, and then ethyl acetate and water were introduced thereto. The mixed solution was filtered to remove solid, and then the filtered liquid was layer-separated. The separated organic layer was washed with an aqueous solution of saturated sodium bicarbonate, dried over sodium sulfate, and then concentrated in vacuo. The concentrated solution was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give an orange solid of 6-methoxynaphthalene-2-amine (77.9 g, 0.450 mmol, 53.3%). 1H-NMR (CDCl3, Varian 400 MHz): delta3.73 (2H, brs), 3.88 (3H, s) , 6.93-6.97 (2H, m) , 7.04-7.08 (2H, m) , 7.51 (1H, d, J=8.8 Hz), 7.57 (1H, d, J=8.8 Hz)

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 2-Bromo-6-methoxynaphthalene.

Reference:
Patent; COLLEGE OF MEDICINE POCHON CHA UNIVERISTY INDUSTRY- ACADEMIC COOPERATION FOUNDATION; CHAMEDITECH CO., LTD.; Yoon, Tae Jong; Chung, Kwang Hoe; Seo, Jeongbeob; Kang, Sin Wook; Lee, Kwang Hyuong; Kwon, Yong Su; Jeon, Hye Sun; Lee, Chae Woon; Kim, Jin sung; US2018/327357; (2018); A1;,
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The important role of (2,4-Dimethoxyphenyl)methanamine

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20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

( 2R,6R, 1 lR)-tert-butyl 8-(( 2,4-dimethoxybenzyl)carbamoyl)-6, 11 -dimethyl-1, 2,5,6- tetrahydro-2, 6-methanobenzo[d]azocine-3( 4H)-carboxylate Chemical Formula: C 38N205 Exact Mass: 494.28 Molecular Weight: 494.62 To a solution of (2R,6R,1 lR)-tert-butyl 6,11 -dimethyl- 8- (((trifluoromethyl)sulfonyl)oxy)-l,2,5,6-tetrahydro-2,6-methanobenzo[d]azocine- 3(4H)-carboxylate (5.32 g, 11.8 mmol) in degassed dimethyl sulfone (50 mL), was added N-hydroxysuccinimide (2.73 g, 23.7 mmol), palladium acetate (265 mg, 1.18 mmol), triethylamine (3.3 mL, 23.7 mmol) and 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (683 mg, 1.18 mmol). The reaction mixture was heated with carbon monoxide (latm) at 70C overnight. The reaction mixture was cooled to ambient temperature and 2,4-dimethoxybenzylamine (2.17 mg, 13.0 mmol) added. The mixture was stirred for 2 hours diluted with ethyl acetate (800 mL), and filtered through celite. The organic solution was washed twice with water (800 mL), brine (300 mL), and dried (MgS04). Filtration and removal of the solvent under reduced pressure gave crude material that was purified by silica chromatography (EtOAc(l):heptanes(l)) to give (2R,6R,llR)-tert-butyl 8-((2,4- dimethoxybenzyl)carbamoyl)-6, 11 -dimethyl- 1 ,2,5,6-tetrahydro-2,6- methanobenzo[d]azocine-3(4H)-carboxylate (4.0 g, 68% yield); LC/MS(M+H)+ = 495.3.

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Reference:
Patent; ALKERMES PHARMA IRELAND LIMITED; BLUMBERG, Laura, Cook; DEAVER, Dan; EYERMAN, David; WO2014/190270; (2014); A1;,
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Continuously updated synthesis method about 2,4-Dibromo-1-methoxybenzene

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.

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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Some scientific research about 6770-38-3

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.

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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Continuously updated synthesis method about 19056-41-8

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.

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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Some scientific research about 74137-36-3

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.

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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