Category: ethers-buliding-blocks

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. 64465-53-8, name is 4-Fluoro-3-methoxyaniline, A new synthetic method of this compound is introduced below., Quality Control of 4-Fluoro-3-methoxyaniline

Dissolve 4-fluoro-3-methoxyphenylamine (5. 0 g, 35 mmol) in water (25 mL) and concentrated sulfuric acid (8 mL). Cool to less than 0 C in an ice/methanol bath and add sodium nitrite (2. 7 g, 39 mmol) dropwise in a solution in water (20 mL) and stir one h. Dissolve potassium iodide (9. 9 g, 60 mmol) in water (35 mL) and add dropwise. Warm to room temperature and stir 18 h. Extract with ethyl acetate (300 mL), wash with water (200 mL), saturated aqueous sodium thiosulfate (300 mL), and saturated aqueous sodium chloride (300 mL). Dry (sodium sulfate), filter, and concentrate to give the title compound as an orange oil (8. 8 g, 99%). H NMR (300 MHz, CDCl3) 6 3. 88 (s, 3H), 6. 77-6. 87 (m, 1H), 7. 16-7. 26 (m, 2H).

The synthetic route of 64465-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
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Application of 64115-88-4,Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, 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: To a microwave vial with stir bar was added 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3,4,5-trimethoxyphenyl)benzo[d]oxazol-2-amine (97 mg, 0.228 mmol), 4-bromo-1H-benzo[d]imidazole (30 mg, 0.152 mmol), DME (1.5 mL), Sodium carbonate (0.76 mL, 1.523 mmol) [2.0M (aq)] and PdCl2(dppf)-CH2Cl2 adduct (12.43 mg, 0.015 mmol). Vial capped and heated in an aluminum tray at 120 C for 3 hr. Reaction mixture was cooled to RT, diluted with water. Aqueous mixture was extracted with EtOAc. Organic phases combined, washed with brine, dried (Na2SO4), filtered and concentrated. Residue dissolved with DMSO and purified by RHPLC. Product fractions combined, frozen and lyophilized to afford a TFA salt of 7-(1H-benzo[d]imidazol-4-yl)-N-(3,4,5-trimethoxyphenyl) benzo[d]oxazol-2-amine (8.1 mg, 0.015 mmol, 9.93 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Article; Costales, Abran; Mathur, Michelle; Ramurthy, Savithri; Lan, Jiong; Subramanian, Sharadha; Jain, Rama; Atallah, Gordana; Setti, Lina; Lindvall, Mika; Appleton, Brent A.; Ornelas, Elizabeth; Feucht, Paul; Warne, Bob; Doyle, Laura; Basham, Stephen E.; Aronchik, Ida; Jefferson, Anne B.; Shafer, Cynthia M.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1592 – 1596;,
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Electric Literature of 645-36-3, These common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, 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.

Compound 3 was prepared by the condensation of commercially available aminoacetaldehyde diethyl acetal with the phthalic anhydride (1:1 mol ratio), using toluene under reflux, in the presence of a catalytic amount of DMAP (yield 52%) for 2 h. In the next step, 2-(2,2-diethoxyethyl)isoindoline-1,3-dione (3) underwent acid hydrolysis (sulphuric acid at 70%) in reflux for 2 h. After the reaction was completed, it was allowed to reach at room temperature and was then cooled to induce precipitation. The formed precipitate was filtered on a sintered funnel with distilled water, yielding 55% of the pure product. For the synthesis of 5a and 5b, 2-(1,3-dioxoisoindol-2-yl) acetaldehyde (4) reacted with thiosemicarbazide (in the ratio 1:1) (for 5a) or 4-phenyl-3-thiosemicarbazide (for 5b), in ethanol, under reflux with catalytic amount of HCl (4 drops) for 4 h. The reactions were followed by thin layer chromatographic plate analysis. The formed precipitate was filtered on a sintered funnel with ethanol to yield the pure product (yield 76% for 5a and 70% for 5b).

Statistics shows that 2,2-Diethoxyethanamine is playing an increasingly important role. we look forward to future research findings about 645-36-3.

Reference:
Article; De Moraes Gomes, Paulo Andre Teixeira; Oliveira, Arsenio Rodrigues; De Oliveira Cardoso, Marcos Verissimo; De Farias Santiago, Edna; De Oliveira Barbosa, Miria; De Siqueira, Lucianna Rabelo Pessoa; Moreira, Diogo Rodrigo Magalhaes; Bastos, Tanira Matutino; Brayner, Fabio Andre; Soares, Milena Botelho Pereira; De Oliveira Mendes, Andresa Pereira; De Castro, Maria Carolina Accioly Brelaz; Pereira, Valeria Rego Alves; Leite, Ana Cristina Lima; European Journal of Medicinal Chemistry; vol. 111; (2016); p. 46 – 57;,
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Application of 7252-83-7, A common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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.

Following a modified procedure,[9] under a N2 atmosphere, 8a (867 mg, 1.44 mmol) andCs2CO3 (3.05 g, 9.36 mmol) were placed in a 100 mL sealed tube. 2-Bromo-1,1-dimethoxyethane (9) (1.60 g, 9.5 mmol) and solvent DMF (30 mL) were added via cannula.The reaction mixture was stirred at 110 C for 24 h. At ambient temperature, the mixture wasdiluted with EtOAc (250 mL) and washed with H2O (3¡Á60 mL) and brine (60 mL). Theorganic phase was dried over Na2SO4 and concentrated. The residue was purified by columnchromatography over silica gel (n-hexane/EtOAc 5/1) to give S10 (804 mg, 81%) as acolorless solid. M. p. = 162-163 C. 1H NMR (300 MHz, CDCl3) delta = 6.92 (s, 1H), 6.91 (s,1H), 6.92-6.78 (m, 4H), 6.79 (d, J = 8.8 Hz, 1H), 6.71 (d, J = 1.1 Hz, 1H), 4.85 (t, J = 5.5 Hz1H), 4.62-4.41 (m, 5H), 3.65 (s, 3H), 3.63 (s, 3H), 3.45 (s, 3H), 3.31 (s, 6H), 1.38 (d, J =6.1 Hz, 6H), 1.33 (d, J = 6.1 Hz, 6H), 1.31 (d, J = 6.1 Hz, 6H). 13C NMR (125 MHz, CDCl3)delta = 155.6 (Cq), 150.1 (Cq), 149.5 (Cq), 147.4 (Cq), 147.2 (Cq), 146.5 (Cq), 146.2 (Cq), 146.1(Cq), 144.0 (Cq), 127.7 (Cq), 127.4 (Cq), 123.8 (CH), 123.4 (CH), 122.2 (Cq), 118.5 (Cq),115.9 (CH), 115.2 (CH), 115.0 (CH), 114.6 (Cq), 114.5 (CH), 110.2 (Cq), 105.3 (CH), 104.4(CH), 103.5 (CH), 71.5 (CH), 71.5 (CH), 71.2 (CH), 55.9 (CH3), 55.8 (CH3), 55.6 (CH3), 55.3(CH3), 47.9 (CH2), 22.1 (CH3), 21.9 (CH3). IR (neat): 2975, 2931, 1703, 1517, 1463, 1257,1107, 1031, 752 cm-1. MS (ESI) m/z (relative intensity) 712 (100) [M+Na+], 690 (50)[M+H +], 658 (80). HR-MS (ESI) m/z calcd for C39H48NO10 [M+H+] 690.3273, found690.3267.

The synthetic route of 7252-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mei, Ruhuai; Zhang, Shou-Kun; Ackermann, Lutz; Synlett; vol. 28; 14; (2017); p. 1715 – 1718;,
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Electric Literature of 145903-31-7, 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. 145903-31-7, name is 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: To a stirred solution of 2-(benzyloxy)ethanol (17.0 g, 1 1 1 .84 mmol) and PPh3 (35.0 g, 134.21 mmol) in DCM (170 mL) at -10 Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68461; (2013); A1;,
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Some common heterocyclic compound, 589-10-6, name is (2-Bromoethoxy)benzene, molecular formula is C8H9BrO, 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: 589-10-6

3)0.24 g (10 mmol) of sodium hydride and 15 ml of N, N-dimethylformamide were added to a 50 ml round bottom flask,Stirred at room temperature for 10 minutes,Another 2.5 g (10 mmol) of compound 2 was addedAnd 10 mmol of 2-phenoxybromoethane,And TLC detection to the end of the reaction,The reaction mixture was then poured into 500 ml of ice water, extracted three times with 100 ml of ethyl acetate,The organic phases are combined, the solvent is evaporated to dryness,The resulting residue was purified by silica gel column chromatography (V dichloromethane: V methanol = 100: 1)Compound 3 (2.3 g, yield 63%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 589-10-6, its application will become more common.

Reference:
Patent; Guangxi Normal University; Chen Zhenfeng; Liang Hong; Liu Yancheng; Lu Xing; Huang Kunyuan; (13 pag.)CN106478677; (2017); A;,
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Related Products of 5414-19-7, A common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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.

The t-butyl ester from Part D (3 g, 6.2 mmol), N,N-Dimethylformamide (15 mL), K2CO3 (2.76 g, 20 mmol), 2-bromoethyl ether, Aldrich, (1.75 g, 7.6 mmol), and 18-Crown-6 (0.49 g, 1.86 mmol) were heated together at 65 C. under an N2 atmosphere overnight. An additional 1 g of K2CO3 (7.2 mmol) and 0.87 g of 2-bromoethyl ether (3.78 mmol) were added to the mixture, and it was again stirred overnight at 65 C. under an N2 atmosphere. The reaction mixture was cooled to ambient temperature, and then added to deionized water (75 mL) and ethyl acetate (200 mL). The layers were separated, and the aqueous layer was back-extracted with ethyl acetate (50 mL). The combined ethyl acetate layers were washed with 100 mL of each of a 1:1 mixture of deionized water:saturated NaCl(aq) and saturated NaCl(aq), dried over MgSO4, filtered, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexanes) produced 1.76 g (51.24%) a t-butyl ester pyran in the form of a solid.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
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Application of 452-08-4, 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. 452-08-4, name is 2-Bromo-4-fluoro-1-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 107 9-Fluoro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 207, structure 41 of Scheme XI, where R1 =H, R2 =F) 5-Fluoro-2-methoxyphenylboronic acid (structure 37 of Scheme XI; where R1 =H, R2 =F) In a 200-mL flask, a solution of 2-bromo-4-fluoroanisole (Aldrich: 4.00 mL, 30.8 mmol) in THF (50 mL) was cooled to -78 C. (CO2 /IPA). To this solution n-BuLi (Aldrich: 2.5M in hexanes; 12.4 mL, 31 mmol, 1.0 equivuiv) was added dropwise over a 30 min period. The reaction mixture was stirred at -78 C. for 60 min and treated with trimethylborate (Aldrich: 10.5 mL, 92.4 mmol, 3.0 equivuiv). The reaction mixture was allowed to slowly warm to rt, stirred overnight (12 h), and cooled to 0 C. (ice/H2 O). The solution was treated with 5% HCl until the pH reached 6. The reaction mixture was poured into sat’d NH4 C80 mL) and extracted with CH2 Cl2 (3*100 mL). The extracts were washed with sat’d NH4 Cl (1*80 mL), combined, dried (MgSO4), filtered through a pad of Celite, and concentrated to afford 4.90 g (94%) of a white semi-solid. Data for 5-fluoro-2-methoxyphenylboronic acid: 1 H NMR (400 MHz, acetone-d6): 7.47 (dd, J =8.8, 3.3, 1 H); 7.17 (m, 1 H); 7.05 (dd, J=9.0, 3.9, 1 H); 3.93 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-fluoro-1-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696133; (1997); A;,
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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. 1579-40-4, name is Di-p-tolyl Ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Di-p-tolyl Ether

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

The synthetic route of 1579-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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Reference of 1462-37-9, 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To N-Boc-L-tyrosinemethyl ester 17 (2 g, 6.8 mmol) indry DMF (20 ml) was added 2 equiv. of 2-bromo-O-benzyl-ethanol (2.9 g, 13.6 mmol) along with 3 equiv. of K2CO3(2.8 g, 20.4 mmol) at room temperature for 1h gave the arylalkyl ether inquantitative yield. The reaction mixture was quenched with ice and extractedwith cold EtOAc (2 x 50 ml). The organic extracts were washed with cold brine(30 ml) and dried over anhydrous Na2SO4. The solvent wasremoved under reduced pressure. The resulting crude product was purified bysilica gel column chromatography using hexanes : EtOAc (9:1) as eluent to givethe 18 (2.5 g) in 87percent yield.1H NMR (CDCl3300 MHz): delta7.4-7.28 (m, 5H), 7.02 (d, J = 8.5 Hz, 2H), 6.85 (d, J = 8.5 Hz, 2H), 4.99-4.91 (m, 0.5H),4.13 (t, J = 4.5Hz, 2H), 3.82 (t, J = 5.1Hz, 2H), 3.7 (s, 3H), 3.1-3.0 (m,2H), 1.42 (s, 9H). 13C NMR (CDCl3, 75 MHz) :delta172.4, 157.8, 155.0, 137.9, 130.2, 128.3, 128.0, 127.7, 127.6, 114.6, 79.8,73.3, 68.4, 67.3, 54.4, 52.1, 37.3, 28.2.IR (KBr): upsilon 2977, 2933, 2873, 1740,1695, 1613, 1585, 1512, 1481, 1392, 1368, 1330, 1248, 1220, 1163, 1072, 963,861, 772, 699 cm-1HRMS (ESI) m/zcalcd for C24H31NO6: 430.2208, found: 430.2224[M+H]+.[alpha]D25: -9.0(c = 1.0, CHCl3).

The chemical industry reduces the impact on the environment during synthesis ((2-Bromoethoxy)methyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kumar, Harish; Reddy, A. Srinivas; Reddy, B.V. Subba; Tetrahedron Letters; vol. 55; 9; (2014); p. 1519 – 1522;,
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