Ethers-buliding-blocks

366-99-4, 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. 366-99-4 name is 3-Fluoro-4-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.

Example 18 Synthesis of (4-Chloro-6-cyclohexylmethoxy-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl)-amine (114) To a sample of 113 (1.011 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solution of 3-fluoro-p-anisidine (0.541 g, 3.8 mmol) in acetone (10 mL) followed by addition of NaOH (1.52 mL, 2.5 N, 3.8 mmol) and water (3 mL). The reaction mixture was allowed to stir at reflux for about 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (silica gel, 70:30 hexanes:ethyl acetate) yielded light yellow solid compound 114 (0.581 g, 42percent), mp 98¡ã C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.36; MS (ESI): m/z 369 (39.1), 368 (22.1), 367 (M+H, 100), 273 (3.2), 271 (10.7). Example 19 Synthesis of 6-Cyclohexylmethoxy-N,N’-bis-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4-diamine (115) [0741] Compound 115 was obtained as a by-product (0.159 g) via column chromatography (silica gel, 70:30 hexanes:ethyl acetate), mp 181¡ã C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.17; MS (ESI): m/z 472 (M+H, 100), 261 (1.5).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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. 5905-69-1

A stirred mixture of l-bromo-4-(difluoromethoxy)benzene (0.54 mL, 4 mmol), bis(pinacolato)diboron (1.21 g, 4.8 mmol), l, -bis(diphenylphosphino)ferrocene- palladium dichloride (0.32 g, 0.4 mmol), and potassium acetate (1.18 g, 12 mmol) in dry 1,4-dioxane (10.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 90 C and monitored with LC- MS and TLC. After 21 h, the reactions were cooled to rt then filtered through celite. The organic solvent was removed under reduced pressure, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield a yellow liquid as 2- (4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolane. 1H NMR (400 MHz, DMSO-de) delta ppm 7.76 (2 H, m), 7.30 (3 H, m), 1.29 (12 H, s).N-(5-(4-(Difluoromethoxy)phenyl)-2-morpholinopyridin-4-yl)-5,7-difluoro-3- methyl-2-(pyridin-2-yl)quinolin-4-amine.

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 5905-69-1.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); A1;,
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The chemical industry reduces the impact on the environment during synthesis 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, I believe this compound will play a more active role in future production and life. 54149-17-6

Example 35 Preparation of N-{2-[2-(2-methoxyethoxy)ethoxy]phenyl}-17-methylmorphinan-3-amine (35), hydrochloride salt (35) Step 1. Synthesis of l-bromo-2-(2-(2-methoxyethoxy)ethoxy)benzene, A mixture of 2-bromophenol (0.448g, 2.59 mmol), l-bromo-2-(2- methoxyethoxy)ethane (0.383mL, 2.85 mmol), and potassium carbonate (1.073g, 7.76 mmol) in dimethyl formamide (5 mL) was stirred at 60 C overnight. The reaction mixture was poured into 20 mL of 5% LiCl solution and extracted with ethyl acetate 3x30mL. The organic layer was washed with brine, was dried over sodium sulfate, was filtered and was concentrated. After drying under high vacuum, the pure product was obtained as colorless oil (656.7 mg) in 92% yield. *Eta NMR (400 MHz, CDCl-3): delta 7.54 (d, 1H), 7.24 (t, 1H), 6.92 (d, 1H), 6.83 (t, 1H), 4.40 (t, 2 H), 3.92 (t, 2H), 3.80 (t, 2H), 3.58 (t, 2H), 3.39 (s, 3H). MS (EI) for CnHi5Br03: 292 (MNH4+).

The chemical industry reduces the impact on the environment during synthesis 54149-17-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
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Adding some certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5. 1535-73-5

General procedure: To a stirred solution of 11 (13.14 mmol) in 1,2-dichloroethane (240 mL) were added appropriate substituted anilines (19.71 mmol) and AcOH (13.14 mmol), and the mixture was heated to reflux for 2 h under nitrogen atmosphere. The reaction mixture was cooled to 0 ¡ãC, and MeOH (60 mL) and THF (20 mL) were added. To it, (AcO)3BHNa (26.20 mmol) or NaBH4 (52.56 mmol) was added portionwise, and then the reaction mixture was allowed to warm to room temperature and stirred for an additional 3 h. The pH of the reaction mixture was adjusted to 7?8 at 0 ¡ãC with 1 NHCl, and then the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2¡Á 300 mL). The combined organic layers was washed with brine (300 mL) and dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel to afford the titled compounds as a solid.

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 3-Trifluoromethoxyaniline.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
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2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 2930-05-4

General procedure: A 50mL sealed tube with a magnetic stirring bar was evacuated and backfilled will CO2 for three times, potassium organoaluminate (0.1mmol), (n-Bu)4NI (0.05mmol), epoxide (2.0mmol), and 1.0mL THF were added. The reaction mixture was stirred at 50C (heating mantle temperature) for 24h. The reaction was then quenched with H2O (10mL) and extracted with ethyl acetate (3¡Á15mL). The combined organic layers were dried over Na2SO4 and concentrated. The yields were determined by 1H NMR spectroscopy with trichloroethylene (90muL, 1mmol) as an internal standard. Then, the reaction mixture was purified on silica gel column chromatography (petroleum ether/EtOAc: 3/1). All cyclic carbonates were identified through comparisons with the corresponding 1H NMR, 13C NMR data reported in the literatures [7].

Statistics shows that 2930-05-4 is playing an increasingly important role. we look forward to future research findings about 2-((Benzyloxy)methyl)oxirane.

Reference:
Article; Guo, Zhiqiang; Yan, Leilei; Liu, Yaoming; Wu, Xiaoqin; Wei, Xuehong; Journal of Organometallic Chemistry; vol. 922; (2020);,
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1462-37-9, A common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)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.

Step A: To a suspension of NaH (688 mg, 27.8 mmol) in THF (80 mL) was added diethyl malonate (7.45 g, 46.5 mmol) dropwise. Then ((2-bromoethoxy)methyl)benzene (5 g, 23.2 mmol) was added. The reaction was heated to 90 ¡ãC for 5 hours. After cooling to room temperature, the mixture was diluted with EtOAc (50 mL), washed with water (50 mL x 2), dried over anhydrous Na2S04 and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with a gradient of 10percent – 30percent EtOAc/hexanes to to afford diethyl 2-(2-(benzyloxy)ethyl)malonate (6.6 g, 22.5 mmol, 81percent yield) as a colorless oil.

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; YUK, Inn H.; PURKEY, Hans; O’BRIEN, Thomas; WO2015/142903; (2015); A2;,
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The chemical industry reduces the impact on the environment during synthesis 21702-84-1, name is 2,4-Dibromo-1-methoxybenzene, I believe this compound will play a more active role in future production and life. 21702-84-1

53.2 g of 2,4-dibromoanisole (B30), 40.4 g of 2-methyl-3-butyn-2-ol, 3.81 g of copper iodide, 150 g of triethylamine, 75 g of tetrahydrofuran, and 14.0 g of bis ( Triphenylphosphine) palladium (II) dichloride was mixed, and the temperature was raised to 60 C and stirred for 7 hours.After cooling to room temperature, filtration was performed, and the filtrate was concentrated under reduced pressure. The obtained oily substance was purified by column chromatography [silica gel (600 g), hexane: ethyl acetate = 2: 1] to obtain 50.9 g of diol. (B31).

The chemical industry reduces the impact on the environment during synthesis 21702-84-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Xin Yue Chemical Industry Co., Ltd.; International Business Ye Machine Corporation; Ju Chengyilang; Du Bianwu; Xin Jingtianhuijie; Chang Jingyangzi; Ze Cunangzhi; Di Yuanqin; Ya Lishanda¡¤aidehua¡¤hesi; Ge Leigeli¡¤buleita; Dan Nier¡¤baoluo¡¤sangdesi; Lu Di¡¤J¡¤woyitaiciji; (58 pag.)CN110627600; (2019); A;,
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4463-59-6, Adding some certain compound to certain chemical reactions, such as: 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene, 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 4463-59-6.

Compound II 0.2g (0.36mmol) dissolved in DMF were added K2CO3 0.1g (0.72mmol), a catalytic amount of TBAB and compound III-6 0.17g (0.72mmol), at 80 C overnight. After completion of the reaction, water was added to the potassium carbonate was dissolved, ethyl acetate (20mL ¡Á 3). The combined organic phases were washed with 1N NaOH ¡Á 2,1N HCl ¡Á 2, with saturated NaCl ¡Á 2, dried over anhydrous Na2SO4 dry. Filtration, column chromatography (petroleum ether: ethyl acetate = 2) to give a white solid IV-6 0.16g, yield: 66.7%.

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 4463-59-6.

Reference:
Patent; CHINA PHARMACEUTICAL UNIVERSITY; HUANG, WENLONG; QIAN, HAI; WANG, XUEKUN; LI, YING; YANG, BAOWEI; LI, ZHENG; (23 pag.)CN103739581; (2016); B;,
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20265-97-8, The chemical industry reduces the impact on the environment during synthesis 20265-97-8, name is 4-Methoxyaniline hydrochloride, I believe this compound will play a more active role in future production and life.

p-Anisidine hydrochloride (23.14 g, 132.5 mmol) was dissolved in ethanol (400 mL) and TRIFLUOROACETALDEHYDE ethyl hemiacetal (20 mL, 172.3 mmol) was added and refluxed overnight. The reaction was concentrated, and the crude compound was redissolved in N, N-dimethylformamide (150 mL) and cooled to 0C. N-BROMOSUCCINIMIDE (23.59 g, 132.5 mmol) was added to the solution over five minutes. The reaction was warmed to rt and stirred overnight. The reaction was quenched with water (1000 mL) and ethyl acetate (5000 mL), extracted with ethyl ACETATE (3X500 ML), WASHED WITH brine (1×500 ML) 7 DRIED OVER NA2804, concentrated, and purified by flash chromatography using 0-10% ethyl acetate/hexanes as eluent afforded 18. 8 g (48%) of the hydrazone intermediate

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

Reference:
Patent; BRYSTOL-MYERS SQUIBB COMPANY; WO2004/83177; (2004); A2;,
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Adding a certain compound to certain chemical reactions, such as: 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, 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 103291-07-2, 103291-07-2

4-Bromo-1-fluoro-2-methoxybenzene a15 (0.0204 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine were added sequentially under argon atmosphere. Ethyl b1 (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated under a 6W blue light lamp at 50 C for 72 h.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 30/1.Yellow liquid (32) (0.0109 g, 94%) was obtained.

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-Bromo-1-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
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