Category: ethers-buliding-blocks

Some common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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: A typical procedure for Suzuki reaction is as follows: arylhalide (0.5mmol) was weighed in 25mL round bottom flask containing boronic acids (0.6mmol), and Pd(OAc)2(PPh3)2/MgCe-HDC (100mg). The reactants and catalyst were dispersed in water (4mL), the RB was mounted on an oil bath at 353K and the mixture was stirred for 2h. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the catalyst was separated by filtration. Then the solution was extracted with ethyl acetate and brine solution. The organic phase was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by column chromatography on silicagel to afford pure product. The pure product was analyzed using 1H- and 13C-NMR techniques and compared with literature NMR data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2398-37-0, its application will become more common.

Reference:
Article; Tomar, Ravi; Singh, Nidhi; Kumar, Neeraj; Tomar, Vartika; Chandra, Ramesh; Catalysis Letters; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 25245-34-5, The chemical industry reduces the impact on the environment during synthesis 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

Example 7: Preparation of 4,4′-dibromo-2,2′,5,5′- tetramethoxybiphenyl (7); [00113] In a 100 ml round-bottom flask, 3.0 g of FeCI3 in 20 ml of CH2CI2 was added to a solution of 5.0 g of 2,5-dimethoxybromobenzene in 50 ml of CH2CI2. The reaction mixture was stirred overnight, and then it was washed with water and brine and dried with magnesium sulfate. The solvent was removed on a rotary evaporator and the residue was purified by column chromatography eluted by hexane/CH2CI2 (3:1) to obtain 3.4 g of 4,4′- dibromo-2,2′,5,5′-tetramethoxybiphenyl (yield 68%) 1HNMR (CDCI3) 57.194 (s, 2 H), 6.841 (s, 2 H), 3.877 (s 3 H), 3.757 (s, 3 H).

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, 2-Bromo-1,4-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NATIONAL UNIVERSITY OF SINGAPORE; WO2006/93467; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A three-neck flask was charged with Pd(OAc)2 (0.0182 mmol, 4.1 mg), BINAP (0.02 mmol, 12 mg) and NaO-t-Bu (1.274 mmol, 122 mg). The reaction mixture was stirred in toluene (20 mL) for 10 min at 80 C. A mixture of NH2CH2CH(OCH2CH3)2 (1.092 mmol, 159 muL) and the compound prepared as in Example 1 (0.91 mmol, 500 mg) in toluene (2 mL) was then slowly added dropwise via syringe to the reaction mixture. After addition, the mixture was heated at 80 C. with stirring for 2 h. The reaction mixture was cooled to room temperature. Et2O and water were added and the solution was partitioned between Et2O and water. The Et2O layer was washed with brine, dried over anhydrous Na2SO4 and concentrate to yield the title compound as a crude solid. The crude product was purified by column chromatography using 4:1 hexanes/EtOAc to yield the title compound as a colorless oil. [0215] 1H NMR (300 MHz, CDCl3) delta 7.12 (d, J=8.8 Hz, 1H), 6.53 (d, J=8.8 Hz, 1H) 6.38 (s, 1H), 4.68 (t, J=6.0 Hz, 1H), 3.80 (br, s, 1H), 3.75 (m, 2H), 3.60 (m, 2H), 3.22 (d, J=6.0 Hz, 2H), 2.91 (m, 2H), 2.50 (dd, J=18.0, 8.8 Hz, 1H), 2.42 (m, 1H), 2.35 (m, 1H), 2.20 (m, 1H), 2.151.94 (m, 3H), 1.721.38 (m, 6H), 1.25 (t, J=7.6 Hz, 6H), 0.98 (s, 3H) MS (m/z) M+Na (408), MH- (384).

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, 2,2-Diethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sui, Zhihua; Zhang, Xuqing; US2005/4090; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, 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.

General procedure: To a solution of compound 11 (100 mg, 0.21 mmol) and 3-methoxybenzeneboronic acid (49 mg, 0.32 mmol) in dioxane (5 mL) and H2O (0.5 mL) was added Na2CO3 (44 mg, 0.42 mmol) and LiCl (18 mg, 0.42 mmol). Under Ar, Pd(PPh3)4 (24 mg, 0.021 mmol) was added. The mixture was stirred for 12 h at 85C. Water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 67 mg of 12 (yield: 75%) as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxy-1-methylbenzene, its application will become more common.

Reference:
Article; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 round bottom flask at room temperature, containing formic acid (85%, 27 rrsL, 624.4 mmoi) was added acetic anhydride (16 mL, 169.5 mmoi) dropwise. The reaction stirred for 45 min. followed by the dropwise addition of a solution of 4-bromo- 2-methoxyaniline (9.01 g, 44.6 mmoi) in THF (56 mL). The reaction mixture was quenched with ice-water after 23 h and the resulting precipitate was filtered to afford compound 100.1 (9.20 g, 90%) as a brown solid.

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; SCHERING CORPORATION; WO2009/76352; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 36865-41-5,Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 ethyl isonipecotate (22.0 grams, 140 mmol) in acetonitrile (250 mL) at room temperature was added cesium carbonate (97 grams, 298 mmol) followed by l-brom -3-methoxypropane (20 mL, 154 mmol) and the reaction mixture was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and filtered through a small pad of celite. The volatiles were removed under reduced pressure to obtain ethyl l-(3-methoxy propyl) piperidin-4-carboxylate (31.0 grams).Yield: 99 %.? – NMR (CDCI3): delta 4.12 (q, 2H), 3.41 (t, J = 6.4 Hz, 2H), 2.90 – 2.85 (m, 2H), 2.38 (t, J = 7.4 Hz, 2H), 2.34 – 2.20 (m, 1H), 2.05 – 1.93 (m, 2H), 1.92 – 1.85 (m, 2H), 1.80 – 1.70 (m, 4H), 1.23 (t, J = 7.1 Hz, 3H); Mass (m/z): 230 (M+H)+.

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-3-methoxypropane, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; MOHAMMED, Abdul Rasheed; YARLGADDA, Suresh; RAVELLA, Srinivasa Rao; SHINDE, Anil Karbhari; KAMBHAMPATI, Ramasastri; ROAYALLEY, Praveen Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; PATNALA, Sriramachandra Murthy; RAVULA, Jyothsna; JASTI, Venkateswarlu; WO2013/42135; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 36865-41-5, A common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 5-bromo-2-chloro-phenol (10.00 g, 48.20 mmol, 1.00 eq), 1-bromo-3- methoxy-propane (14.75 g, 96.41 mmol, 2.00 eq) and K2C03 (19.99 g, 144.61 mmol, 3.00 eq) in acetone (100.00 mL) was stirred at 50 C for 15 h. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with PE to PE :EA=5: 1. 4-bromo- 1 -chloro-2-(3 -methoxypropoxy)benzene (13.40 g, 47.93 mmol, 99.44% yield) was obtained as a colorless oil which was confirmed by LC-MS and used directly in the next step. LC-MS: EW5403-239-P1ZO (M+H=278.9, M+2+H=280.9)

The synthetic route of 36865-41-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (81 pag.)WO2018/22282; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 62257-15-2, name is 2-Fluoro-5-methoxyaniline, 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 62257-15-2, Safety of 2-Fluoro-5-methoxyaniline

B. Ethyl 5-amino-1-(2-fluoro-5-methoxyphenyl)-1H-imidazole-4-carboxylate, 3b A solution of compound 3a (4.5 g, 35 mmol) and (diethoxymethoxy)ethane (6.3 g, 42 mmol) in CH3CN (50 mL) was stirred at 80 qC for 1 h. The reaction mixture was allowed to cool to RT and treated with 2-fluoro-5-methoxyaniline (3.0 g, 21 mmol). The resulting solution was stirred overnight at RT and concentrated. The residue obtained was purified by flash chromatography (0-25% EtOAc/petroleum ether) on silica gel to obtain compound 3b as a light yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C13H14FN3O3: 280.1 (M+H); found: 280.0.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (196 pag.)WO2017/27310; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 54314-84-0

The reaction mixture of 28 (0.50 g, 1.5 mmol) and [(3-bromopropoxy)methyl]benzene (32) (0.44 ml, 2.5 mmol) in dry 1,4-dioxane (16 ml) was stirred for 5 days to afford the title compound as a white solid in 73% yield (0.62 g). mp: 228-229 C; 1H-NMR (400 MHz, DMSO-d6): delta = 7.27-7.40 (m, 15H), 6.76 (s, 1H), 5.21 (br, 1H), 4.46 (s, 2H), 3.85 (m, 1H), 3.46 (t, J = 5.8 Hz 2H), 3.21-3.39 (m, 6H), 3.03 (m, 1H), 2.25 (m, 1H), 1.49-1.95 (m, 6H); 13C-NMR (500 MHz, DMSO-d6): delta = 172.8, 158.9, 143.6, 143.5, 130.1, 128.5, 128.4, 128.2, 128.1, 127.6, 127.5, 121.1, 115.0, 81.3, 69.1, 67.0, 63.0, 59.8, 54.1, 53.2, 26.2, 23.9, 20.9, 19.0, 18.1; HRMS calcd. for C31H36N1O4 [M]+: 486.2644; found: m/z = 486.2663; HPLC (Method B): tR (min) = 15.2 (98%).

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; Yamashita, Yasunobu; Tanaka, Ken-ichiro; Yamakawa; Asano; Kanda, Yuki; Takafuji; Kawahara, Masahiro; Takenaga, Mitsuko; Fukunishi, Yoshifumi; Mizushima; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3339 – 3346;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 366-99-4, A common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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 1. To a mixture of 3-fluoro-4-methoxyaniline (3.00 g, 21.3 mmol) and paraformaldehyde (1.28 g, 42.5 mmol) in MeOH (100 mL) was added sodium methoxide (19.4 mL, 85.0 mmol) and the reaction mixture mixture was sealed and heated at 55 °C for 2 h. After cooling to rt, sodium borohydride (2.01 g, 53.1 mmol) was added in small portions. The final reaction mixture was stirred at rt overnight. The solvent was removed in vacuo and the residue was taken up in EtOAc (100 mL) and washed with water (150 mL). The separated aqueous component was saturated with NaCl, extracted with EtOAc (100 mL) and the combined organic components were washed with brine (50 mL), dried over MgS04, filtered, and concentrated in vacuo. The residue was taken up into DCM (10 mL) and purified by FCC (80 g silica gel cartridge), eluting with gradient 5percent~50percent EtO Ac- hexanes to afford 3-fluoro-4-methoxy-N-methylaniline (3.08 g) as a light yellow oil. LC- MS retention time = 1.34 min; m/z = 153.42 [M-H]-. (Start percent B = 0, Final percent B = 100, Gradient Time = 2 min, Flow Rate = 1 ml/min, Wavelength = 220, Solvent Pair = Water: Acetonitrile 10 mM Ammonium Acetate, Solvent A = 95percent Water: 5percent Acetonitrilel 10 mM Ammonium Acetate, Solvent B = 5percent Water: 95percent Acetonitrile 10 mM Ammonium Acetate, Column = Phenomenex Luna CI 8 2.0 X 30mm 3um, MW1 = 132+/- Oven Temp. = 40 °C).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem