Tag: M.W=200-300

Application of 63057-72-7, The chemical industry reduces the impact on the environment during synthesis 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, I believe this compound will play a more active role in future production and life.

At room temperature, 1-Benzyloxy-4-bromo-2-methoxybenzene 10 (1.70 mmol, 0.50 g) was dissolved in freshly distilled THF (7 mL) in an oven-dried three-neck flask under argon. The temperature was cooled down to -78 oC and n-BuLi (1.6M in hexane, 1.96 mmol, 1.22 mL) was added dropwise. The reaction mixture was stirred for 1 h at this temperature and a solution of 4-benzyloxy-3-methoxybenzaldehyde 9 (1.70 mmol, 0.412 g) in THF (4mL) was added dropwise. The reaction mixture was stirred at -78 oC for 1.5 h, allowed to warm at room temperature and stirred for another 2 h. Water (24 mL) was slowly added to the mixture which was then extracted three times with EtOAc. The organic layers were dried with MgSO4 and concentrated in vacuo. The crude product was dissolved in a minimum of EtOAc and 100 mL of hexanes were added to precipitate the desired product. After 12 h at 0 oC, the precipitate was filtered, lightly washed with cold EtOAc and dried in vacuo, yielding 0.618 g (79 %) of 11 as a white solid. mp = 94-100oC. 1H-NMR (500 MHz, CDCl3): deltaH7.46-7.29 (10H,m), 6.96-6.79 (6H,m), 5.72 (1H, s), 5.13 (4H, s), 3.86 (6H, s). 13C-NMR (125 MHz, CDCl3): deltaC 149.7, 149.5, 147.6, 137.2, 135.4, 128.6, 127.9, 127.3, 119.7, 119.7, 118.9, 113.7, 113.5, 111.0, 110.3, 75.7, 71.0, 56.0. IR (ZnSe): numax 1511, 1251, 1226, 1132, 1019, 1006, 754, 741, 696 cm-1. HRMS (ESI-TOF,m/z): calcd for C29H27O4 (M-H2O+H)+= 439.1904, found 439.1923. This compound has been also previously reported.4

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-(Benzyloxy)-4-bromo-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cardinal, Sebastien; Azelmat, Jabrane; Grenier, Daniel; Voyer, Normand; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 440 – 444;,
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Electric Literature of 101-55-3,Some common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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.

Nanoporous metal gold catalyst (9.8 mg, 0.05 mmol),Ethanol (1.5mL) and 4-bromophenyl phenyl ether(62.27mg, 0.25mmol),Cesium carbonate (364.3 mg, 1.125 mmol) was added to the reaction vessel, and hydrogen (40 bar) was introduced.Heating and stirring, the reaction temperature is controlled at 100 C,The reaction time is controlled at 90h.The reaction solution is extracted with water,Obtained 39.1 mg of biphenyl,The yield was 92%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-phenoxybenzene, its application will become more common.

Reference:
Patent; Dalian University of Technology; Bao Ming; Zhao Yuhui; Feng Xiujuan; Yu Xiaoqiang; Zhang Sheng; (13 pag.)CN109608297; (2019); A;,
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Application of 20469-65-2, These common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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 dichloromethane solution (300 mL) of 1-bromo-3.5-dimethoxaybenzene (8.00 g, 36.9 mmol) in ice bath was added BBr3 (25.00 g, 100 mmol) dropwise. After 2 hours, themixture was allowed to warm to room temperature and stirred over night. Methanol (10 mL) was added dropwise to terminate the reaction. The mixture was poured into water and stirred for 2 hours, then saturated sodium bicarbonate (100 mL) was added and extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate, brine, and then dried over Na2SO4 The residue, after concentration, was purified using chromatography(eluent: methoh/DCM: 2/98, v/v). A white solid (1.0 g) was obtained as product. LC-MS and HNMR are nice.

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLCEUTIX CORPORATION; FAN, Xiaodong; XU, Yongjiang; LIU, Dahui; COSTANZO, Michael J.; WO2014/93225; (2014); 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 19056-40-7 as follows. Application In Synthesis of 4-Bromo-3-methoxyaniline

Sodium nitrite (8.54 g, 123.7 mmol) dissolved in water (100 ml) was added to an ice- cold suspension of 4-bromo-3-methoxyaniline (25 g, 123.7 mmol) in concentrated HCl (46 ml, 1514 mmol) and water (100 ml). After stirring for 10 minutes, 2-cyanoacetamide (10.40 g, 123.7 mmol) and sodium acetate trihydrate (84 g, 617 mmol) in water (1.8 L) was added and the reaction was allowed to stir overnight. The resulting solid was collected by filtration, washed with water, dried, giving an orange solid which was refluxed in 1.4 L of ethanol for 30 min. The mixture was cooled to room temperature, the solid was collected by filtration, washed with ethanol (100 ml x 3), and dried to yield the title compound as a yellow solid (34.4 g, 94 percent). 1H NMR: 11.70 (s, 1 H), 7.90 (s, 1 H), 7.50 (m, 2 H), 7.35 (s, 1 H), 7.20 (d, 1 H), 3.90 (s, 3 H); m/z: 296

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/136191; (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.

General procedure: General synthetic procedure for the final products.The appropriately substituted 4-phenethylpiperidine (6)(0.5 mmol) was dissolved in acetonitrile (5 mL) and K2CO3(0.75 mmol) and the appropriate phenethyl bromide (7) (0.5 mmol) added. The reaction mixture was refluxedfor 8 h.After completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambient temperature and filtered through a Celite pad. The filtrate was concentrated under vacuum to obtain the desired crude product. The crude product was further purified by column chromatography (silica gel: 3-5% methanol in dichloromethane) to afford the corresponding 1,4-diphenethylpiperidine (8a-8y) in good yield (75-80 %), which was then converted to hydrochloride salt by treatment with 2M HCl in diethyl ether.Compounds12a-12dwere synthesized using the same procedure as above, except that an appropriately substituted 4-benzylpiperidine (11) was utilized in place of compound6.

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

Reference:
Article; Nickell, Justin R.; Culver, John P.; Janganati, Venumadhav; Zheng, Guangrong; Dwoskin, Linda P.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 2997 – 3000;,
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Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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 1462-37-9, Recommanded Product: ((2-Bromoethoxy)methyl)benzene

To a solution of 3-hydroxybenzaldehyde (2.90 kg, 23.75 mol), and ((2- bromoethoxy)methyl)benzene (4.26 kg, 19.79 mol) in DMF (9.3 L) was added K2C03 (3.83 kg, 27.70 mol). The reaction mixture was stirred at r.t. for 24 h. Water (15 L) and tert-butyl methyl ether (23 L) were added to the reaction mixture. The organic phase was separated and washed with 1 N NaOH (2X15 L) and water (15 L) sequentially, and then concentrated to a minimum. Ethanol (23 L) was added and the solution was concentrated under vacuum to afford the desired product (4.7 kg, 93percent) as a colourless oil. 1 H NMR (400 MHz, DMSO-c/6): 9.98 (s, 1 H), 7.55-7.52 (m, 2H), 7.46 (s, 1 H), 7.36-7.34 (m, 4H), 7.32-7.26 (m, 2H), 4.57 (s, 2H), 4.25-4.22 (t, J = 4.4 Hz, 2H), 3.80-3.78 (t, J = 4.4 Hz, 2H). LCMS: [M+Na]+ = 279

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ANACOR PHARMACEUTICALS, INC.; ALLEY, M.R.K. (Dickon); HERNANDEZ, Vincent S.; PLATTNER, Jacob J.; LI, Xianfeng; BARROS-AGUIRRE, David; GIORDANO, Ilaria; WO2015/21396; (2015); A2;,
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Reference of 32338-02-6, 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. 32338-02-6, name is 2-Bromo-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 °C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

The synthetic route of 2-Bromo-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Electric Literature of 2132-62-9, The chemical industry reduces the impact on the environment during synthesis 2132-62-9, name is 1,2-Bis(4-methoxyphenyl)ethyne, I believe this compound will play a more active role in future production and life.

6-chloro-1-(4-chlorophenyl)-3,4-bis(4-methoxyphenyl)-1H-2,1-benzoxaphosphinine 1-oxide (69.1 mg, 88%) as a target product was obtained under the condition of 90 C. for 16 hours, by the same reaction as the Example 1 above, except for using bis(4-chlorophenyl)phosphinic acid (43.0 mg, 0.15 mmol) instead of using phenylphosphonic monoethyl ester of the Example 1 above, and using 1,2-bis(4-methoxyphenyl)ethyne (53.6 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 1 above. (0218) 1H NMR (400 MHz, CDCl3) delta 7.87-7.81 (m, 2H), 7.52-7.44 (m, 3H), 7.29 (td, J=8.1, 2.1 Hz, 1H), 7.17-7.14 (m, 4H), 7.05 (dd, J=4.1, 4.8 Hz, 1H), 6.95 (app d, J=8.7, 2H), 6.67-6.63 (m, 2H), 3.87 (s, 3H), 3.73 (s, 3H).

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, 1,2-Bis(4-methoxyphenyl)ethyne, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KNU-INDUSTRY COOPERATION FOUNDATION; Lee, Phil Ho; Park, Young Chul; Jeon, In Cheol; Seo, Jung Min; Seo, Bo Ram; US2015/344506; (2015); A1;,
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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 1663-61-2 as follows. Quality Control of (Triethoxymethyl)benzene

General procedure: Method A (synthesis of imidazol-5(4H)-ones 7) ? The appropriate alpha-aminocarboxylic acid hydrazide 5 (10 mmol) was added to a mixture of triethyl orthoester (30 mmol), dry xylene (40 mL) and 0.12 g p-TsOH and kept under reflux until the disappearance of the starting hydrazide 5 was completed (2-20 h). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude product was purified by column chromatography with silica gel and an eluent of benzene/AcOEt, 1:3 v/v or MeOH/CHCl3, 1:4 v/v.

According to the analysis of related databases, 1663-61-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Jasiak, Karolina; Tetrahedron Letters; vol. 54; 35; (2013); p. 4637 – 4640;,
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Reference of 588-63-6, A common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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.

tert-BuLi (12 mL of a 1.7 M solution, 20 mmol) was added dropwise to a solution of 4-bromo-N,N-dimethylaniline (2.00 g, 10 mmol) in THF (40 mL) at 78° C. The resulting solution was stirred at 78° C. for 1 hour and was then warmed to ambient temperature. Tellurium powder (1.28 g, 10 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 1 hour. 1-Bromo-3-phenoxypropane (2.04 g, 9.5 mmol) in 5 mL of THF was added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was filtered through Celite and the filter cake was washed with CH2Cl2 (50 mL). The filtrate was concentrated and the residue was partitioned between H2O (100 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted with additional CH2Cl2 (3*25 mL). The combined organic extracts were dried over MgSO4 and concentrated. The crude product was then purified by column chromatography on silica gel eluted with 60percent CH2Cl2/hexanes to give 1.9 g (52percent) of 23b as an orange oil: 1H NMR (400 MHz, CDCl3) 7.63 (d, 2H, J=8.8 Hz), 7.24 (t, 2H, J=7.8), 6.91 (t, 1H, J=7.2), 6.84 (d, 2H, J=8.0 Hz), 6.54 (d, 2H, J=8.8 Hz), 3.97 (t, 2H, J=6.0 Hz), 2.94 (s, 6H), 2.90 (t, 2H, J=7.4 Hz), 2.20 (quint, 2H, J=6.8 Hz); 13C NMR (75 MHz, CDCl3) delta 158.9, 150.3, 141.2, 129.4, 120.6, 114.5, 113.4, 94.7, 68.7, 40.2, 31.2, 4.3; High Resolution MS (EI) m/z 385.0694 (Calcd for C17H21NO130 Te: 385.0681). Anal. Calcd for C17H21NOTe: C, 53.32; H, 5.53; N, 3.66. Found: C, 53.26; H, 5.61; N, 3.32.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Research Foundation of State University of New York; US2008/26027; (2008); A1;,
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