Author: Jessica.F

These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, 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

Intermediate 1: 2-propyl-4-(trifluoromethoxy)aniline A solution of 2-bromo-4-(trifluoromethoxy)aniline (256 mg, 1.00 mmol), [(E)-prop-1-enyl]boronic acid (172 mg, 2.00 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (29.0 mg, 0.0400 mmol), and K2CO3(aq) (1 M, 2 equiv) in MeOH (0.5 mL)/toluene (0.5 mL) was stirred at 125 C. for 4 h. The organic layer was separated, concentrated to dryness, and purified by FCC (SiO2) to give (E)-2-(prop-1-en-1-yl)-4-(trifluoromethoxy)aniline. (E)-2-(Prop-1-en-1-yl)-4-(trifluoromethoxy)aniline and Pd/C (10% on carbon, 30 mg) in MeOH (10 mL) was stirred under H2 (1 atm) for 3 h. After filtration on diatomaceous earth such as Celite, the filtrate was collected and concentrated to dryness to give 2-propyl-4-(trifluoromethoxy)aniline. MS (ESI): mass calcd. for C10H12F3NO, 219.1; m/z found, 220.1 [M+H]+.

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

Reference:
Patent; Janssen Pharmaceutica NV; Bacani, Genesis M.; Chai, Wenying; Edwards, James P.; Smith, Russell C.; Tichenor, Mark S.; Venable, Jennifer D.; Wei, Jianmei; (64 pag.)US2018/289706; (2018); A1;,
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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. 588-96-5, name is p-Bromophenetole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: p-Bromophenetole

To a solution of 2R-allyl-3S-hydroxy-succinic acid diisopropylester (4.79 g, 18.5 MMOL), 4-bromo PHENETOLE (3.19 MI, 22.2 mmol, 1.2 eq. ) and NEt3 (6.22 ML, 44.6 MMOL, 2.4 eq. ) in CH3CN (40 ml), was added a sonicated (for 2 min) suspension of P (O-TOL) 3 (0.57 g, 2.22 mmol, 0.1 eq. ) and Pd (OAC) 2 (209 mg, 5%) in CH3CN (5 ML). The reaction mixture was heated to reflux for 2 hrs. CH3CN was removed under vacuum. The crude was extracted with AcOEt (3 X 200 ML), washed with water (50 mi) and with brine (50 ML). A purification by flash chromatography afforded the desired 2R- [3- (4-ethoxy-phenyl)-allyl]-3S- hydroxy-succinic acid diisopropyl ester (5.92 g, 84% yield). 1H-NMR ; delta (CDC13), 7.28 (2H, d, J = 8.8Hz), 6.83 (2H, d, J = 8.8Hz), 6.46 (1H, d, J = 15.7Hz), 6.02-6. 12 (1H, m), 4.98-5. 13 (2H, m), 4.26 (1H, dd, J = 7.1, 3. 0HZ), 4.02 (2H, q, J = 7. 0HZ), 3.23 (1H, d, J = 7. 1 HZ), 2.92-2. 97 (1H, m), 2.68-2. 79 (1H, m), 2.49-2. 62 (1H, m), 1.41 (3H, t, J=7.0 Hz) and 1.19- 1.30 (12H, m). LRMS: +ve ion 400 (M+Na).

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRITISH BIOTECH PHARMACEUTICALS LTD; LABORATOIRES SERONO S.A.; WO2004/101537; (2004); A1;,
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Electric Literature of 910251-11-5, 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. 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl (R)-12′-(benzyloxy)-H’-chloro-8′-oxo- ,2′,8′,13b’-tetrahydrospiro[cyclopropane-l,3′- pyrido[2,l-a]pyrrolo[l,2-c]phthalazine]-7′-carboxylate (234 mg, 0.51 mmol) was dissolved in isopropanol (10 mL) with 2 drops of acetic acid. The mixture was stirred at reflux for 2.5 hours, then cooled to room temperature to provide isopropyl (R)-12′-(benzyloxy)-H’-chloro-8′-oxo- ,2′,8′,13b’-tetrahydrospiro[cyclopropane-l,3′-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine]-7′- carboxylate. MS (m/z) 491.3 [M+H]+. The crude ester was combined with (0993) trifluoro(methoxymethyl)-borane, potassium salt (230 mg, 1.52 mmol), Pd RuPhos G4 (52 mg, 0.061 mmol), RuPhos (42 mg, 0.091 mmol), and cesium carbonate (823 mg, 2.53 mmol) in toluene:water (3: 1, 5 mL) under argon in a sealed vial. The mixture was heated at 110 C for 45 minutes with vigorous stirring, then cooled to room temperature, the aqueous layer was removed, and the organics were concentrated in vacuo and purified by flash column (0994) chromatography (hexanes / ethyl acetate / ethanol / triethylamine) to provide isopropyl (R)-12′- (benzyloxy)-i -(methoxymethyl)-8′-oxo- ,2′,8′,13b’-tetrahydrospiro[cyclopropane-l,3′- pyrido[2,l-a]pyrrolo[l,2-c]phthalazine]-7′-carboxylate. MS (m/z) 501.4 [M+H]+.

The synthetic route of Potassium trifluoro(methoxymethyl)borate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CANALES, Eda; CURRIE, Kevin S.; KATO, Darryl; LI, Jiayao; LINK, John O.; METOBO, Samuel E.; SAITO, Roland D.; SCHROEDER, Scott D.; SHAPIRO, Nathan; TSE, Winston C.; WU, Qiaoyin; (262 pag.)WO2018/144605; (2018); 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 349-65-5 as follows. Formula: C8H8F3NO

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy) aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

According to the analysis of related databases, 349-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CORPORATION; US2002/165394; (2002); A1;,
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Synthetic Route of 1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

A mixture of triethyl orthoformate (92 ML, 0.55 mol) and 2, 2-DIMETHYL- [1, 3] – dioxane-4,6-dione (75.3 g, 0.522 mol) (Meldrum’s acid) was heated at 55 °C for 90 minutes and then cooled to 45 °C. A solution of 3-benzyloxyaniline (100.2 g, 0.5029 mol) in methanol (200 mL) was slowly added to the reaction over a period 45 minutes while maintaining the reaction temperature below 50 °C. The reaction was then heated at 45 °C for one hour, allowed to cool to room temperature, and stirred overnight. The reaction mixture was cooled to 1 °C, and the product was isolated by filtration and washed with cold ethanol (-400 mL) until the filtrate was colorless. 5-F [ (3- Benzyloxy) phenylimino] METHYL}-2, 2-dimethyl- [1, 3]-dioxane-4, 6-dione (170.65 g) was isolated as a tan, powdery solid. 1H NMR (300MHZ, DMSO-D6) : 8 11. 21 (d, J= 14. 2 Hz, 1H), 8.61 (d, J= 14.2 Hz, 1H), 7.49-7. 30 (m, 7H), 7.12 (dd, J= 8.1, 1.96 Hz, 1H), 6.91 (dd, J= 8.4, 2.1 Hz, 1H), 5.16 (s, 2H), 1. 68 (s, 6H).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2005/20999; (2005); A1;,
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Related Products of 651734-54-2, These common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-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.

A mixture of 2,4-dichloro-5-(iodomethyl)pyrimidine (1.50 g, 5.19 mmol), 2,6- difluoro-3,5-dimethoxyaniline (1.08 g, 5.71 mmol) in N,N-diisopropylethylamine (4 mL) was stirred at 80 C for 2 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel (eluting with 0- 40% EtOAc in DCM) to give 1.70 g of the desired product. LCMS calculated for C13H12CI2F2N3O2 [M+H]+ m/z: 350.0; Found: 350.0.

Statistics shows that 2,6-Difluoro-3,5-dimethoxyaniline is playing an increasingly important role. we look forward to future research findings about 651734-54-2.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; WU, Liangxing; QIAN, Ding-Quan; YAO, Wenqing; (102 pag.)WO2016/134314; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22483-09-6, name is 2,2-Dimethoxyethanamine, 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 22483-09-6, Safety of 2,2-Dimethoxyethanamine

General procedure: A solution of amino acetaldehyde dimethyl acetal 2a (10. 514 g, 1.081 mL, 10 mmol), purchased from Alfa Aesa, and an aldehyde (10 mmol) in dry ethanol was placed in a round bottom flask and stirred for 12 h. To that solution, sodium borohydride powder (0.567 g, 15 mmol) was added at 0 C slowly over 5 minutes. the solution was then warmed to room temperature. After stirring for 4 h, the reaction was quenched with 3 drops of water and the mixture was filtered through a pad of celite. The solvent was evaporated under reduced pressure, the residue was extracted with 100 mL of ethyl ether and washed with100 mL of water. The organic layer was dried over MgSO4 anhydrous. Ethyl ether was then evaporated and the resulted viscous liquid was purified by flash column chromatography (SiO2; 4:1 then 3:1 and finally 1:1hexanes/ethyl acetate).

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:
Article; Luu, Quang H.; Guerra, Jorge D.; Castaneda, Cecilio M.; Martinez, Manuel A.; Saunders, Jong; Garcia, Benjamin A.; Gonzales, Brenda V.; Aidunuthula, Anushritha R.; Mito, Shizue; Tetrahedron Letters; vol. 57; 21; (2016); p. 2253 – 2256;,
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Synthetic Route of 62257-15-2,Some common heterocyclic compound, 62257-15-2, name is 2-Fluoro-5-methoxyaniline, molecular formula is C7H8FNO, 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.

E. Preparation of N-benzyl-2-fluoro-5-methoxyaniline This procedure was patterned after that of Tietze and Grote, Chem Ber. 126(12), 2733 (1993). A solution of 2.73 g of 2-fluoro-5-methoxyaniline and 2.67 g of benzaldehyde in 48 ml of methanol was treated with 3.43 g of zinc chloride and then cooled in an ice bath. Sodium cyanoborohydride (1.58 g) was added in small poroom temperature ions over 30 minutes and the reaction was stirred for five hours at room temperature. After evaporation of the solvent, the residue was slurried in 40 ml of 1 N sodium hydroxide solution and then extracted twice with ether. The extracts were washed with water and then with brine, dried over magnesium sulfate and concentrated. The residue was recrystallized from hexane to afford 2.61 g and the mother liquors were chromatographed on silica gel using 20:1 hexane/ether to afford another 1.4 g of the subtitle compound (90%). mp. 56-58C

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-5-methoxyaniline, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; EP950657; (1999); A2;,
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Some common heterocyclic compound, 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, molecular formula is C7H5BrF2O, 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. Recommanded Product: 4-Bromo-2,6-difluoroanisole

The mixture of 5-bromo-l,3-difluoro-2-methoxy-benzene (2.6 g, 11.7 mmol), ethynyl (trimethyl)silane (1.145g, 11.7 mmol), N,N-Diisopropylethylamine (1.205 g, 9.33 mmol), Copper(I)Iodide (177.6 mg, 0.93 mmol) and Bis(Triphenylphosphine)palladium (II) chloride (340.4 mg, 0.47 mmol) in THF (20 mL) were heated at 60 C under a nitrogen atmosphere for 16 hours. Added water (50 mL) and extracted by EtOAc (60 mL), washed EtOAc phase with water (50 mL), brine (50 mL), dried over Na2S04, filtered and concentrated to give a residue. The residue was purified by slica gel column (pure PE) to afford the title compound as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104197-14-0, its application will become more common.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); A1;,
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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. 2398-37-0, name is 1-Bromo-3-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2398-37-0

1-Bromo-3-methoxybenzene (20 mmol), CH2Cl2 (50 mL) and CH3COCl (1.5 eq., 30 mmol) were added to a 250 mL round-bottom flask. After cooled to -20 oC, AlCl3 (3 eq., 8.0 g) was added to the mixture slowly. The reaction was stirred vigorously for 3 h at -20 oC. Ice water ( 80 mL ) was added to the flask and the mixture was extracted with CH2Cl2 (30 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 1-(2-bromo-4-methoxyphenyl)ethanone, yield 75%.

The synthetic route of 2398-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lou, Zhen-Bang; Pang, Xin-Long; Chen, Chao; Wen, Li-Rong; Li, Ming; Chinese Chemical Letters; vol. 26; 10; (2015); p. 1231 – 1235;,
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