Category: ethers-buliding-blocks

35736-52-8, name is 2,4-Dibromo-5-methoxyaniline, 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. Quality Control of 2,4-Dibromo-5-methoxyaniline

2,4-Dibromo-5-methoxyaniline (930 mg, 3.31 mmol) and paraformaldehyde (160 mg, 5.30 mmol) were dissolved in trifluoroacetic acid (30 mL). The reaction mixture was stirred under an argon atmosphere in dark for 48 h. The reaction mixture was then basified with a solution of concentrated ammonia (30 mL) in water (30 mL). A saturated sodium hydrogen carbonate solution (100 mL) was added and the aqueous mixture was extracted into dichloromethane (3×50 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed (silica, dichloromethane) to afford (+/-)-18 (450 mg, 53%) as a pale off-white solid: mp 181-182 C; Rf (CH2Cl2) 0.22; IR (neat) numax 2938, 2895, 2848, 1604, 1486, 1442, 1420, 1247, 1195, 1082 cm-1; 1H NMR (400 MHz, CDCl3) delta 3.74 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.15-4.33 (m, 4H, CH2), 4.47 (d, J 17.0 Hz, 1H, CH2), 4.52 (d, J 17.0 Hz, 1H, CH2), 6.66 (s, 1H, ArH), 7.09 (s, 1H, ArH), 7.61 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) delta 54.1, 55.3, 56.2, 60.2, 66.5, 107.1, 108.3, 111.5, 114.7, 120.8, 125.5, 131.0, 134.6, 145.4, 147.4, 153.5, 155.0; Anal. Calcd for C17H15Br3N2O2.0.1 CH2Cl2: C 38.93; H 2.90; N 5.31. Found: C 38.85; H 2.73; N 5.06%.

The synthetic route of 35736-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Malik, Qasim M.; Ijaz, Sadia; Craig, Donald C.; Try, Andrew C.; Tetrahedron; vol. 67; 32; (2011); p. 5798 – 5805;,
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Related Products of 330-93-8, The chemical industry reduces the impact on the environment during synthesis 330-93-8, name is 4,4′-Oxybis(fluorobenzene), I believe this compound will play a more active role in future production and life.

Step 1 2-Bromo-l , 1 -dimethoxypropaneOMeBr[00297] A solution of propanal (12 5 mL, 170 mmol) m MeOH (85 mL) is stirred at rt and molecular sieves (3 A, powdered, 4 3 g) are added The mixture is heated at reflux, Br2 (8 8 mL, 170 mmol) is added dropwise over 30 mm and reflux is then continued for 4 5 h The mixture is stirred overnight at rt and K2CO3 (11 9 g, 86 mmol) is then added and the resulting slurry is stirred for 2 5 h This is filtered and the solid is washed with MeOH (20 mL) B?ne (100 mL) is added to the filtrate and the mixture is extracted with pentane (3 x 75 mL) The extracts are d?ed over MgSO4 and evaporated under reduced pressure to afford a pale yellow oil (16 0 g) which is not purified further

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, 4,4′-Oxybis(fluorobenzene), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
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Synthetic Route of 126940-10-1, 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. 126940-10-1, name is 1-Fluoro-3-(methoxymethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound 2 (25 g, 130.2mmol, 1 .Oeq) in dry THF (250ml_) and dry cyclohexane (40ml_) was added sec-BuLi (121.82ml_, 195.3mmol, 1.5eq) drop wise at -78 C under argon. The mixture was stirred for 2h at the same temperature, then compound 3 (62ml_, 520.3mmol, 4. Oeq) was added with sitrring for 10mins at the same temperature. TLC analysis indicated formation of a polar spot then the reaction mass was quenched with satd. NH4CI solution; the reaction mixture was dissolved in ether (2X500mL) and washed with brine (2 x 200mL) & water (2x200mL). The separated organic layer was dried over Na2S04 and concentrated under reduced pressure to give a crude product; which was purified by column chromatography (silica gel 100- 200mesh) using 1 % EtOAc petroleum ether as an eluent to give compound 4 ( 20g, 45.1 % ) as a pale yellow color liquid.

The chemical industry reduces the impact on the environment during synthesis 1-Fluoro-3-(methoxymethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; PRAKESCH, Michael; JOSEPH, Babu; MORIN, Justin-Alexander; (441 pag.)WO2019/153080; (2019); 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. 13985-15-4, name is 2,3,6,7-Tetramethoxy-9,10-dimethylanthracene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C20H22O4

Under an inert N2 atmosphere, 91 (2 g, 6.1 mmol), NBS (4 g, 22.6 mmol) and ABCN (73 mg, 0.3 mmol) were dissolved in anhydrous dichloromethane (150 mL), and the mixture stirred at reflux for 4 hours. The mixture was then cooled to 0 C and filtered. The solid was then dried under high vacuum to afford 92 (2.1 g, 4.3 mmcl, 71%) as a bright yellow solid. 1H NMR (400 MHz, CDCI3) O 4.11 (s, 12H, C(1)H), 5.35 (s, 4H, C(6)H), 7.40 (s, 4H, C(3)H), 13C NMR (100 MHz, CDCI3) 28.7(06), 56.0 (Cl), 101.8(03), 125.7(05), 125.9(04), 150.1 (02).

According to the analysis of related databases, 13985-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZIYLO LIMITED; DAVIS, Anthony; TROMANS, Robert; WILSON, Miriam Ruth; ORCHARD, Michael Glen; CHAPMAN, Andrew Michael; TOMSETT, Michael Roger; MATLOCK, Johnathan Vincent; (320 pag.)WO2018/167503; (2018); 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. 2050-47-7, name is 4,4′-Oxybis(bromobenzene), This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4,4′-Oxybis(bromobenzene)

All manipulations were performed under an inert atmosphere of nitrogen. A Schlenk flask equipped with a condenser was charged with 4- bromophenylether (3.90 g), carbazole (4.34 g), 18-crown-6 (0.70 g), Cu (1.65 g) and K2CO3 (3.60 g) and 1, 2-dichlorobenzene (150 mL). The resulting mixture was heated to 180 C for four days. After cooling to room temperature, water was added and the mixture was stirred overnight. The organic layer was isolated and the water layer was washed with water. The combined organic layers were dried over MgSO4 and the solvent was evaporated to give a brown oil. The desired product was isolated by crystallization from CH2CI2/MeOH to give an off-white powder in 58% yield (3. 5 g) 1H NMR (CD2CI2, 500 MHz): 6 8.14 (d, 1H), 7. 58 (d, 1H), 7.42 (m, 2H), 7.35 (d, 1H), 7.27 (m, 1H).

According to the analysis of related databases, 2050-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E.I. DUPONT DE NEMOURS AND COMPANY; WO2005/82851; (2005); A2;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 10075-63-5, name is 1,5-Dimethoxynaphthalene, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H12O2

70% Nitric acid (1.5 mL) in acetic acid (1.5 mL) was addedslowly to a stirred suspension of 1,5-dimethoxynaphthalene(3.76 g, 20 mmol) in acetic acid (50 mL) at room temperature. Upon stirring overnight atambient temperature, the precipitate was filtered offand washed with water. The crude product wasrecrystallized from methanol and dried. Light yellowsolid, yield 85%. 1H NMR spectrum, delta, ppm: 3.92 s(3H), 4.03 s (3H), 6.74 d (J = 8.3 Hz, 1H), 7.01 d (J =7.8 Hz, 1H), 7.44-7.53 m (2H), 7.90 d (J = 8.5 Hz,1H). 13C NMR spectrum, delta, ppm: 56.03, 56.06, 102.24,108.31, 114.68, 117.16, 121.65, 127.15, 127.21,141.18, 153.64, 157.04.

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:
Article; Dong; Zhang; Huang; Meng; Li; Russian Journal of General Chemistry; vol. 87; 4; (2017); p. 837 – 841; Zh. Obshch. Khim.; vol. 87; 4; (2017); p. 837 – 841,5;,
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Related Products of 2338-54-7, These common heterocyclic compound, 2338-54-7, name is 4-Fluoro-3-methylanisole, 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 vigorously stirred mixture [OF 4-FLUORO-3-METHYLANISOLE] (12.0 g, 85.6 mmol) and pyri- dine (41.7 g, 527 mmol) in water (170 mL) at [50C] was added portion-wise potassium per- manganate (44.65 g, mmol) and then maintained at this temperature for 2 h. The resulting mixture was then allowed to cool to RT and allowed to stand overnight and then heated for a further 5 h at [50C.] Then the mixture was filtered over celite and then the residue was washed with sulfuric acid (conc. 100 mL). The combined filtrates were then [HALF-EVAPORA-] ted and neutralised with potasssium carbonate. Then the mixture was washed with diethyl ether and then the aqueous layer was acidified with hydrochloric acid (conc.) and the pro- duct extracted with diethyl ether. The combined extracts were then dried over sodium sul- phate. After filtration and evaporation the crude solid was [RECRYSTALLISED] from 1,2,-di- chloroethane to afford the title compound (4.4 g, 30%) as a light pink solid. MS [M/E =] 168.9 (M-H). Alternatively, a solution of 4-fluoroanisole (500 mg, 4.0 mmol) in THF (10 mL) was added to a cooled [SOLUTION (-78C) OF 2,] 2,6, 6-tetramethylpiperidine (1.1 g, 7.9 mmol) and BuLi (5 mL, 1.6 M in hexanes, 7.9 mmol) in THF (10 mL) at a slow rate to maintain the tempera- ture [BELOW-70C.] The mixture was maintained at this temperature for 12 h, and then dry C02 gas was passed into the solution. The resulting mixture was allowed to warm up to 0C and then HCl (1 M, 10 mL) was added and the product was extracted with diethyl ether. The combined organic extracts were then dried over sodium sulfate, washed with water and brine, filtered and evaporated. The crude solid was then partioned between sodium hydroxide [(1] M, 10 mL) and diethyl ether. The aqueous phase was then acidified with HCl (1 M) and the product extracted with diethyl ether. Evaporation afforded the title compound (268 mg, 40%) as a white solid. MS m/e = 168.9 (M-H).

Statistics shows that 4-Fluoro-3-methylanisole is playing an increasingly important role. we look forward to future research findings about 2338-54-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/14856; (2004); A1;,
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These common heterocyclic compound, 40515-89-7, name is Phenethoxybenzene, 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. category: ethers-buliding-blocks

General procedure: etherCatalytic decomposition of phenethyl phenyl ether (PPE) to aro-matics was carried out in a stainless steel autoclave reactor (25 mL)under hydrogen atmosphere. Prior to the reaction, each catalystwas reduced using an ex-situ reduction system at 450C for 4 hunder 5% H2/N2flow (50 mL/min). 50 mg of reduced catalyst, 0.25 gof phenethyl phenyl ether (Frinton Laboratory, a reactant), and 9 mLof hexadecane (Sigma-Aldrich, a solvent) were charged into thereactor at room temperature. The reactor was purged with nitro-gen several times in order to remove air. The catalytic reaction wasperformed at 250C and 10 bar (H2) for 3 h with agitation speed of250 rpm. After the reaction, reaction products were analyzed usinga gas chromatograph (Younglin, YL6100) equipped with a DB-1 col-umn and a flame ionization detector (FID). Conversion of phenethylphenyl ether and selectivity for aromatic product (benzene, phe-nol, or ethylbenzene) were calculated according to the followingequations on the basis of mole balance. Yield for aromatic product(benzene, phenol, or ethylbenzene) was calculated by multiplyingconversion of phenethyl phenyl ether and corresponding productselectivity

The synthetic route of Phenethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Jeong Kwon; Lee, Jong Kwon; Kang, Ki Hyuk; Lee, Jong Won; Song, In Kyu; Journal of Molecular Catalysis A: Chemical; vol. 410; (2015); p. 184 – 192;,
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Electric Literature of 1036724-54-5, 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 1036724-54-5 as follows.

Six reactions were carried out in parallel and combined for work-up. To a solution of the product of the previous step (200 g, 711 mmol) in THF (100 mL) was added potassium carbonate (197 g, 1.4 mol). The reaction mixture was purged with nitrogen 3 times, followed by addition of Pd(dppf)Cl2-CH2Cl2 (11.6 g, 14.2 mmol). The reaction mixture was cooled to 0 C., diethylzinc (1 M, 1.07 L) was added drop-wise, and the reaction mixture was stirred at 70 C. for 1 h. The reactions were combined, cooled to 20 C. and poured into water (7 L) slowly. To the mixture was added aq. 4 M HCl to pH 6. The organic layer was separated, and the aqueous phase was extracted with EtOAc (3×2 L). The combined organic layer was washed with brine (5 L), dried over sodium sulfate, concentrated, and purified through a silica gel pad (eluted with 50:1 petroleum ether:EtOAc)) to give the title intermediate (900 g, 92% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.29-7.43 (m, 5H), 6.94-6.97 (m, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.70 (m, 1H), 5.09 (s, 2H), 2.52-2.58 (m, 2H), 1.17 (t, J=7.6 Hz, 3H).

According to the analysis of related databases, 1036724-54-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fatheree, Paul R.; Jiang, Lan; US2020/131178; (2020); A1;,
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Electric Literature of 115929-62-9, These common heterocyclic compound, 115929-62-9, name is 3-Bromo-2,5-dimethoxyaniline, 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: In a round bottom flask equipped with a magnetic stirring bar, 0.3mmol of alpha-formyl-beta-carboline (1a) and 0.3mmol of aniline (2a) in 4mL of [Bmim][BF4] was stirred for 12min. Into this reaction mixture were added 0.35mmol of phenylacetylene (3a) and 10mol% of La(OTf)3 and then heated around 95-100C. After completion of the reaction, as indicated by the TLC, water was added and extracted with ethylacetate. The organic layer was dried over anhydrous Na2SO4. The solvent was concentrated under the reduced pressure. Product was purified by column chromatography on silica gel (eluent: Hexanes/ethyl acetate): Colorless solid, 126 mg, 74%, Rf=0.52 (20% EtOAc/Hexanes), mp: 277-279 C; IR (KBr): 3356, 2939, 2841, 1259, 1107, 744, 545 cm-1; 1H NMR (400 MHz, CDCl3, TMS) delta: 12.51 (1H, s), 9.01 (1H, s), 8.77 (1H, s), 8.28 (1H, d, J=7.7 Hz), 7.76-7.78 (1H, m), 7.69 (1H, t, J=7.4 Hz), 7.40-7.45 (6H, m), 6.99 (1H, s), 4.31 (3H, s), 4.08 (3H, s), 3.56 (3H, s); 13C NMR (100 MHz, CDCl3, TMS) delta: 166.7, 156.3, 153.2, 149.7, 147.2, 143.3, 141.9, 141.3, 137.3, 137.2, 136.9, 130.8, 129.2, 128.3, 127.2, 127.1, 122.1, 121.6, 121.3, 120.9, 119.0, 118.9, 116.7, 112.3, 110.3 (aromatic C), 61.6, 55.7, 52.6 (aliphatic C); HRMS (ESI-MS) calcd for C30H22BrN3O4; 590.0692 (M+Na), found: 590.0692. Anal. Calcd for: C, 63.39; H, 3.90; N, 7.39%; found: C, 63.25; H, 3.98; N, 7.21%.

Statistics shows that 3-Bromo-2,5-dimethoxyaniline is playing an increasingly important role. we look forward to future research findings about 115929-62-9.

Reference:
Article; Ramesh, Subburethinam; Nagarajan, Rajagopal; Tetrahedron; vol. 69; 24; (2013); p. 4890 – 4898;,
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