Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 589-10-6, name is (2-Bromoethoxy)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 589-10-6, Computed Properties of C8H9BrO

(E)-ethyl 3-(l-(2-phenoxyethyl)-lH-pyrazol-4-yl)acrylateCesium carbonate (0.490g, 1.5 mmol) and l-(2-bromoethoxy)benzene (0.261 g, 1.30 mmol) were added to a solution of (E)-ethyl 3-( H-pyrazol-4-yl)acrylate (0.167 g, 1 mmol) in ACN (8 mL) at room temperature. The suspension was stirred overnight at 80C. The reaction mixture was then cooled down to room temperature and the precipitated solids were filtered off. The filtrate was concentrated and purified by silica gel column chromatography using a gradient of 0-60% of EtOAc in hexanes to provide the title compound (0.203g, 71%) as a colorless oil. ES+ (M+H)+ 287

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; REPLIGEN CORPORATION; JACQUES, Vincent; RUSCHE, James R.; PEET, Norton P.; SINGH, Jasbir; WO2012/118782; (2012); 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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of (Trimethoxymethyl)benzene

General procedure: To a stirred solution of the respective N-carbamate-protected aminovicinal diol 4 (0.50 mmol, 1 equiv) in CH2Cl2 (10 mL, 0.05 M) were added BF3·OEt2 (50 muL, 0.050 mmol, 0.1 equiv, 1.0 M solution in CH2Cl2) and trimethyl orthobenzoate (0.13 mL, 0.75 mmol, 1.5 equiv) at r.t. The resulting mixture was refluxed or stirred at r.t. under N2 until TLC showed complete conversion of the substrate. The reaction was quenched with sat. aq NaHCO3 and extracted with EtOAc (2 ×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane/EtOAc) to give the desired product 5.

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Park, Heemin; Kwon, Yongseok; Shin, Jae Eui; Kim, Woo-Jung; Hwang, Soonho; Lee, Seokwoo; Kim, Sanghee; Synthesis; vol. 49; 12; (2017); p. 2761 – 2767;,
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Electric Literature of 19500-02-8, The chemical industry reduces the impact on the environment during synthesis 19500-02-8, name is 3-Methoxy-2-methylaniline, I believe this compound will play a more active role in future production and life.

The imidate salt 2g2 (1.5g, 7.65mmol) was combined with 2-methyl-3-aminoanisole 2a2 (1.05g, 7.65mmol, 1 eq.) in ethanol (15 ml) under an N2atmosphere. The reaction mixture was stirred at R.T. (24 h) and monitored by HPLC.The reaction mixture was concentrated and then ether was added and the mixturefiltered. The solids were washed with ether and the combined ether washesconcentrated in vacuo. The resulting adduct 2m1 was purified by chromatography(SiO2, 15percent EtOAc/hexanes) to obtain as a yellow oil (2.11g, 99percent). MS electrospray:(M + H)+; 280 and (M – H)-; 278.

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, 3-Methoxy-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37895-73-1, name is 1,2-Dibromo-4,5-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 37895-73-1, Formula: C8H8Br2O2

A 10 mL of a 1.6 M n-BuLi solution and 50 mL ofabsolute tetrahydrofuran were charged into a Schlenk flask (250 mL), the flask was cooled down to -20C,and a solution of 4.7 g (15.9 mmol) of 1,2-dibromo-5,6-dimethoxybenzene in 30 mL of absolute tetrahydrofuranwas added within half an hour ensuring thatthe temperature of the mixture did not exceed -20C.After stirring, a preliminarily prepared solution of3.53 g (16 mmol) of chlorodiphenylphosphine in20 mL of absolute tetrahydrofuran was added dropwisewithin an hour. Then the cooling was removed,and it was allowed to warm up to room temperature. A sample for GC-MS was collected (having preliminarytreated the mixture by a solution of sodium bicarbonate).The analysis showed the presence of 81% targetproduct of the total weight of the dry organic residuein the mixture. The solution was evaporated to dryness,and methanol was added to the residue. A viscousyellow precipitate was formed. The solvent wasevaporated, and diethyl ether was added. A fine whiteprecipitate was formed. The formed precipitate wasground, filtered off, and dried. Yield 3.82 g (60%). 1H NMR spectrum (300 MHz,CD2Cl2): delta (ppm) 7.42 (t, J = 3.5 Hz, 8H, Ar-H),7.08-7.03 (m, 12H, Ar-H), 6.82 (s, 2H, Ar-H), 3.18(s, 6H, OCH3). 31P{1H} spectrum (121.49 MHz,CDCl3): delta (ppm) -12.73 (s, PPh2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Dibromo-4,5-dimethoxybenzene, and friends who are interested can also refer to it.

Reference:
Article; Cheredilin; Sheloumov; Senin; Kozlova; Afanas?ev; Bespalova; Petroleum Chemistry; vol. 59; (2019); p. S72 – S87; Neftekhimiya;,
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Reference of 36865-41-5, These common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, 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 stirred solution of [2], X=Br (1 wt, 1 mol eq.) in DMF (5 vol.) was added (0229) portionwise CS2CO3 (2.34 wt, 1.5 mol eq.) at room temperature, and then the reaction mixture was continued on stirring for 10 min. Then, l-bromo-3-methoxypropane (0.65 wt, 1.2 mol eq.) was added dropwise to the reaction mixture at room temperature and stirred for 16 h at the same temperature. The reaction was monitored by TLC. After completion of reaction, the resultant reaction mixture was diluted with water (3.2 vol.), and stirring was continued for 30 min to produce the solid, which was filtered, washed with water and dried under reduced pressure to obtain the product 5-bromo-2-chloro-3-(3-methoxypropoxy)pyridine [3], X=Br as off-white solid. 1H-NMR [300MHz, DMSO-d6]: d 8.10 (d, 1H, J= 1.5 Hz), 7.87 (d, 1H, J= 1.5 Hz), 4.15 (t, 2H, J= 6.0 Hz), 3.45(t, 2H, J= 6.4 Hz), 3.22 (s, 3H), 1.95 (quint, 2H, 7=6.4, 12.4 Hz).

Statistics shows that 1-Bromo-3-methoxypropane is playing an increasingly important role. we look forward to future research findings about 36865-41-5.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; CHEN, Shuai; DORSEY, Bruce D.; GOTCHEV, Dimitar B.; NGUYEN, Duyan; PALLERLA, Mahesh Kumar; PAMULAPATI, Ganapati Reddy; (76 pag.)WO2019/200109; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5, Safety of p-Bromophenetole

General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product.

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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ma, Hengchang; Bao, Zhikang; Han, Guobin; Yang, Ningning; Xu, Yufei; Yang, Zengming; Cao, Wei; Ma, Yuan; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 3; (2013); p. 578 – 584;,
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Reference of 27060-75-9, 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry, stir bar-equipped, 3-neck 250 mL round bottom flask was fitted with a reflux condenser and put under nitrogen. 77 1-bromo-4-methoxy-2-methylbenzene (1.39 mL, 2.011 g, 10.0 mmol, 1.00 eq), 121 CCl4 (20.0 mL, 0.50 Molar, not degassed), 122 N-bromosuccinimide (recrystallized, 2.67 g, 15.0 mmol, 1.50 eq), and 123 benzoyl peroxide (0.121 g, 0.50 mmol, 5 mol %) were added by briefly removing a septum while under positive nitrogen pressure. The reaction was heated to reflux for 18 hours. (0187) The next day, the reaction was filtered through a silica gel plug, rinsing with 10/1 Hex/Et2O. The crude product was purified by normal phase column chromatography (5 cm diameter, 300 mL silica gel, isocratic 4/1 Hex/DCM), giving SI-3 as a fluffy, slightly off-white powder (1.404 g, 5.015 mmol, 50% yield). (0188) 1H NMR (500 MHz, CDCl3) delta 7.45 (d, J=8.8 Hz, 1H), 6.99 (d, J=3.0 Hz, 1H), 6.74 (dd, J=8.8, 3.0 Hz, 1H), 4.56 (s, 2H), 3.80 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 159.28, 137.90, 134.06, 116.67, 116.27, 114.85, 55.71, 33.61. HRMS (EI+) Calculated for C8H8OBr2: 277.89422; Found: 277.89402.

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-4-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Board of Trustees of the University of Illinois; BURKE, Martin D.; CROUCH, Ian; LEHMANN, Jonathan; PALAZZOLO, Andrea; SIMONS, Claire; US2018/305381; (2018); A1;,
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Synthetic Route of 52189-63-6,Some common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, molecular formula is C8H9FO2, 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.

Example 53 3- {4- [3-Fluoro-5- (2-phenoxy-4-trifluoromethyl-phenoxy)-phenoxy]-2-methyl-phenyl}- propionic acid Step A 3-Fluoro-5-methoxy-phenol A-78 C solution of l-fluoro-3, 5-dimethoxybenzene (4. 98 g, 31.9 mmol) in dry CH2C12 (50 mL) is treated with a 1 M CH2C12 solution of boron tribromide (128 mL, 128 mmol), and the mixture is warmed to 0 C and stirred under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. The organic layer is dried (Na2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 2.40 g (53%) of the title compound. Rf= 0.49 (1/1 hexanes/EtOAc).’H NMR (400 MHz, CDCl3). MS (ES-) m/z mass calculated for C7H702F 142, found 141 (M-1,100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37763; (2005); A1;,
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Synthetic Route of 103-50-4, 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 103-50-4 as follows.

General procedure: To a test tube charged with CuCl (2.0 mg, 0.02 mmol) andisochroman (1a; 251 muL, 2.0 mmol) in t-BuOH (20 mL) wasadded TBHP (5.0-6.0 M in decane, 10.9 muL, 0.6 mmol) and themixture was stirred and heated at 50 C for 12 h under open air.After cooling to room temperature, the reaction was quenchedwith 25% aqueous ammonia solution and water then themixture was extracted with EtOAc. The separated organic layerwas dried over Na2SO4 and products were concentrated after filtration.The residue was purified by silica gel column chromatography(EtOAc/hexane, 1:10) to give isochromanone (2a) as acolorless oil in 83% yield.

According to the analysis of related databases, 103-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tanaka, Hirotaka; Oisaki, Kounosuke; Kanai, Motomu; Synlett; vol. 28; 13; (2017); p. 1576 – 1580;,
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Electric Literature of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 8-bromo-6-chloroimidazo[l,2-b]pyridazine-3-carbonitrile (2.82 g, 13.23 mmol), l-(4-methoxyphenyl)-N-methylmethanamine (2.00 g, 13.23 mmol) and diisopropylethylamine (4.62 mL, 26.5 mmol) in tetrahydrofuran (25 mL) was heated to 60 °C for 3 hours and then concentrated to dryness. The crude product was triturated with methanol and filtered rinsing with methanol. The solid was dried and collected as is (3.85 g, 89percent yield). NMR (400MHz, CHLOROFORM-d) delta 7.99 (s, 1H), 7.16 (d, J=8.8 Hz, 2H), 6.93 – 6.82 (m, 2H), 6.12 (s, 1H), 5.45 (br. s., 2H), 3.80 (s, 3H), 3.20 (br. s., 3H). LC retention time 1.05 min [J]. MS (E+) m/z: 328 (MH+).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
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