Category: ethers-buliding-blocks

Application of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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 7252-83-7, Recommanded Product: 2-Bromo-1,1-dimethoxyethane

To a mixture of 4-chloro-6-aminobenzene-1,3-disulfonamide (Aldrich, 15.2 g, 53.3 mmol) and bromoacetaldehyde dimethylacetal (6.3 mL, 9 g, 53.3 mmol) in anhydrous dioxane (45 mL) at 120 C., was added dropwise 48% hydrobromic acid in H20 (2 mL). The mixture was then heated at 100 C. for 20 minutes. The residue, after evaporation of the solvent, was diluted with water, the resultant precipitate was filtered, washed with water to give a sticky solid that was dissolved in EtOAc and dried over Na2SO4. The residue after evaporation of the solvent was recrystallized from EtOAc/hexane to give the title compound in quantitative yield as a white solid: mp 203-205 C.; 1H NMR (400 MHz, d6-DMSO) delta 8.16 (br s, 1H), 8.08 (br d, J=11.2Hz, 1H), 7.99 (s, 1H), 7.53 (br s, 2H), 7.05 (s, 1H), 4.88-5.03 (m, 1H), 3.65-3.72 (m, 2H); 13C NMR (100 MHz, d6-DMSO) delta 146.1, 134.7, 128.9, 125.3, 118.4, 117.4, 66.3, 31.5; Mass spectrum (API-TIS) m/z 387/389 (M-H), 407/409 (MNH4+); Anal. calcd for C8H9BrClN3O4S2. EtOAc: C, 25.41; H, 2.50; N, 10.46; Found: C, 25.35; H, 2.44; N, 10.46.

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

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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, COA of Formula: C9H11BrO

To a solution of methyl 4-hydroxyphenylacetate (500 mg, 3.01 mmol) in N,N-dimethylformamide (2.0 ml), cesium carbonate (1.00 g, 3.07 mmol) and benzyl 2-bromoethyl ether (0.5 ml, 3.2 mmol) were added, and the mixture was stirred at 50°C for 2 hours and then cooled to room temperature. Distilled water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water, dried, and then concentrated under a reduced pressure. The residue was purified via flash chromatography (silica gel, n-hexane/ethyl acetate) to give a title compound (679 mg, 2.26 mmol, 75 percent) as a colorless liquid. 1H-NMR (400 MHz, CDCl3) delta: 3.56 (2H, s), 3.68 (3H, s), 3.82 (2H, t, J = 4.88 Hz), 4.14 (2H, t, J = 4.88 Hz), 4.63 (2H, s), 6.88 (2H, d, J = 8.5 Hz), 7.18 (2H, d, J = 8.5 Hz), 7.27-7.39 (5H, m).

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; TORAY INDUSTRIES, INC.; EP2009006; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 20469-65-2, 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. To a solution of 1-bromo-3,5-dimethoxybenzene (3.01 g, 13.9 mmol) in dry THF (25 mL) at -78C under argon was added a solution of n-BuLi (2.2 M in hexanes, 7.00 mL, 15.4 mmol) dropwise and the mixture stirred for 40 mm. A solution of iodine in dry THF (20 mL) was then added dropwise and the reaction allowed to stir for an additional 45 mm at -78C before quenching with 20% aqueous Na25203 (45 mL) and warming to room temperature. The mixture was diluted with EtOAc (50 mL), the layers separated and the organic layer washed with brine (50 mL), dried (Mg504) and concentrated to a yellow solid (3.12 g). Purification of the crude product by chromatography on silica gel (20% EtOAc/hexanes) gave 1-iodo-3,5- dimethoxybenzene (Compound No. 31, 2.01 g, 55%) as a white solid.

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

Reference:
Patent; AQUINOX PHARMACEUTICALS INC.; MACKENZIE, Lyoyd, F.; MACRURY, Thomas, B.; HARWIG, Curtis; BOGUCKI, David; RAYMOND, Jeffery, R.; PETTIGREW, Jeremy, D.; KHLEBNIKOV, Vladimir; SHAN, Rudong; WO2014/110036; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 175278-09-8, 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. 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 58 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile 4-Bromo-2-(trifluoromethoxy)aniline (1.3 g, 5.0 mmol), 5-cyano-1-methyl -1H-pyrrol-2-ylboronic acid (0.9 g, 6.0 mmol), potassium fluoride (0.96 g, 16.5 mmol), and tris(dibenzylideneacetone)dipalladium (0.12 g, 0.12 mmol) were placed in an oven dried flask under nitrogen and THF (12.5 mL) was added. Tri-t-butylphosphine (10 wt % in hexane) (0.356 mL, 0.24 mol) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica, rinsed with ethyl acetate, and concentrated. The crude product was pre-adsorbed onto the Celite reagent and purified via Isco chromatography (the Redisep column, silica, gradient 5-30% ethyl acetate in hexane) to afford 1.0 g (71%) of 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile. HPLC purity 98.2% at 210-370 nm, 9.6 min.; the Xterra RP18 instrument, 3.5mu, 150*4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. PH=3.5/ACN+MeOH) for 10 min., hold 4 min. MS (ES) m/z 281.

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

Reference:
Patent; Wyeth; US2007/27201; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, 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 2674-34-2, Product Details of 2674-34-2

Reacting a compound of formula 4 with sodium hydride in tetrahydrofuran as a solvent at -78 C for two hours,At the same time, the compound of formula 5 was reacted with n-butyllithium using tetrahydrofuran as a solvent at -78 C for one hour, and then mixed at -78 C for two hours.Add N, N-dimethylformamide and stir for five minutes, add methyl iodide to react at room temperature for twelve hours, add water to quench the reaction,The crude product was subjected to column chromatography with ethyl acetate and petroleum ether system to obtain intermediate formula 6 required for Suzuki Coupling Reaction, with a reaction yield of 52%.

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, 1,4-Dibromo-2,5-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; University of the Chinese Academy of Sciences; Cong Huan; Fan Yangyang; (9 pag.)CN110272332; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

4-Isopropoxy-phenylamine (11.3 g) was added to a solution of 4-hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester (11.5 g) in toluene (361 ml). The mixture was stirred for 10 minutes at RT. Then, dimethylaluminiumchloride (0.9 M in hexane, 99 ml) was added dropwise and the reaction mixture was heated to reflux for 4 h. The mixture was then cooled to 0 C., water (50 ml) was added dropwise then AcOEt (300 ml). The mixture was stirred further 30 minutes, more AcOEt was added, the layers were then separated, the organic layer was dried over MgSO4, filtered and the solvent was evaporated off. The crude product was triturated with diethyl ether/heptane to give the title compound as a mixture of cis/trans isomers as brown solid (14.3 g) which was used directly in the next step. MS (m/e): 304.190 [MH+].

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunziker, Daniel; Neidhart, Werner; US2012/238594; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 658-89-9, The chemical industry reduces the impact on the environment during synthesis 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

Intermediate 73: (Trans)-lambda/-{2-amino-5-[(trifluoromethyl)oxy1phenyl)-3-(2-methylphenyl)-2- oxo-1-oxa-3-azaspiro[4.51decane-8-carboxamide; To a mixture of (trans) 3-(2-methylphenyl)-2-oxo-1-oxa-3-azaspiro[4.5]decane-8- carboxylic acid (Intermediate 72, 150 mg, 0.518 mmol), {2-amino-4- [(trifluoromethyl)oxy]phenyl}amine (prepared in a similar manner to Intermediate 32, 149 mg, 0.778 mmol) and pyridine (0.126 ml, 1.555 mmol) in anhydrous DCM, EDC. HCI was added and the resulting mixture was stirred at room temperature for 1.5 hour. The mixture was diluted with DCM, washed with saturated NaHCO3 solution, dried over Na2SO4 and concentrated under vacuum to give a residue. The residue was purified by silica gel chromatography eluting in gradient from 20% up to 30% Et2ODCM to afford the title compound as yellowish solid (122 mg, 45%). 1 H-NMR (400 MHz, DMSO-d6): delta 1.55-1.70 (m, 2H), 1.70-1.82 (m, 2H), 1.90-2.03 (m, 2H), 2.06-2.17 (m, 2H), 2.20-2.27 (s, 3H), 3.83 (br s, 2H), 5.25 (br s, 2H), 6.46 (d, 1 H), 6.67 (br s, 1 H), 7.21-7.41 (m, 5H), 9.1 1 (br s, 1 H); UPLC-MS: 0.74 min, mz 464 [M+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, 4-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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. COA of Formula: C4H8Br2O

Step a Intermediate 207 -Bromophenyl 2-ethyltetrahydro-2H-pyran-4-carboxylate A mixture of NaH (60% in mineral oil) (2.057 g, 51.4 mmol) in DMF (67 ml) stirred at 0 C was treated dropwise with a mixture of ethyl 2-(4-bromophenyl)acetate (5 g, 20.57 mmol) and 1 -bromo-2-(2-bromoethoxy)ethane (2.59 ml, 20.57 mmol) in 3 ml of diethyl ether. The mixture was allowed to warm to r.t. and stirred for 17 h. Mixture was quenched with water and sat. NH4CI. The mixture was extracted with EtOAc (x 3) and then organics washed with brine (x 3) and dried (MgS04), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02; 0 – 100 % EtOAc in petrol) to yield 4-bromophenyl 2-ethyltetrahydro-2H-pyran-4- carboxylate as a pale yellow oil (2.88 g, 45 %). ? NMR (400 MHz, CD2C12) 57.46 – 7.56 (m, 2H), 7.32 (m, 2H), 4.15 (m, 2H), 3.84 – 3.98 (m, 2H), 3.50 – 3.63 (m, 2H), 2.38 – 2.56 (m, 2H), 1.95 (m, 2H), 1.21 (m, 3H)

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 13321-74-9, These common heterocyclic compound, 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, 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: A flask containing LiCl (980 mg,23.1 mmol), 2-bromo-4-fluoroanisole (1.0 mL, 7.7 mmol), DCMA (1.8 mL,8.4 mmol) and ethyl 3-ethoxyacrylate (3.3 mL, 23 mmol) in 1,4-dioxane(20 mL) was degassed by passing a stream of nitrogen through the mixturefor 10 min. Bis(tri-t-butylphosphine) palladium(0) (166 mg, 0.32 mmol) wasadded, and reaction mixture was heated at reflux under nitrogen for 16 h. Thebrown mixture was then cooled and partitioned between ethyl acetate andwater. The layers were separated, and the organic layer was washedsequentially with aqueous NH4Cl and brine, followed by drying over Na2SO4.The mixture was filtered, and the filtrate was concentrated under reducedpressure to give an oil which was purified by flash chromatography on silica(40 g, 10-50% ethyl acetate in heptane) to afford 22c as an orange oil (1.93 g,92%) as an inseparable mixture of E- and Z-isomers: 1H NMR (CDCl3, 500 MHz)alkene protons d: 5.21, 5.33 ppm (1:1 ratio); LCMS (ES): 269.2 (MH). HRMSCalcd for C14H17FO: 269.1184. Found: 269.1196.

The synthetic route of 13321-74-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kohrt, Jeffrey T.; Conn, Ed; Maguire, Robert; Wright, Stephen W.; Singer, Robert; Tetrahedron Letters; vol. 54; 51; (2013); p. 7065 – 7068;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem