Category: ethers-buliding-blocks

A common compound: 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 126-38-5

To a mixture of 3-bromobenzenethiol (8.7 g, 46 mmol) and l -bromo-2,2- dimethoxypropane (8.4 g, 46 mmol) in NN-dimethylformamide (50 mL) was added potassium carbonate (9.5 g, 69 mmol) at room temperature. The mixture was stirred at 80 C overnight. On completion, the reaction mixture was quenched with water and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude compound B-287 (13 g, 97% yield) as a colorless oil.

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, 126-38-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
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446-59-3, A common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, molecular formula is C7H6BrFO, 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: The 2-bromo-1-ethoxy-4-fluoro-benzene (0.1 mol) was dissolved in THF (25 ml). The solution was cooled to -75 C and a solution of n-BuLi (9.73 ml, 2.4 M in hexane) was added slowly. The mixture was stirred for 30 min at -75 C. Trimethylborate (0.1 mol) was added within 5 min. Acetic acid (0.1 mol) and a 30% solution of H2O2 (0.1 mol) were added sequentially. The mixture was stirred for 30 min at 0 C and for 3 h at room temperature. Water was added and the mixture was extracted with ethyl acetate. The crude product was purified by column chromatography to yield the objected compound.

The synthetic route of 446-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Heng; Xu, Xiangqing; Chen, Yin; Qiu, Yinli; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen; European Journal of Medicinal Chemistry; vol. 89; (2015); p. 524 – 539;,
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136-90-3,Some common heterocyclic compound, 136-90-3, name is 4-Methoxy-3-methylphenylamine, molecular formula is C8H11NO, 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.

c) 2-Hvdroxyimino-Lambda/-(4-methoxy-3-methylphenyl)acetamideChloral hydrate (11.5 g, 70 mmol) and anhydrous sodium sulfate (60 g, 422 mmol) were added to vigorously stirred water (300 ml_). A slurry prepared by mixing hydroxylamine5 hydrochloride (23.0 g, 331 mmol) and 4-methoxy-3-methylphenylamine (10.0 g, 73 mmol) with aqueous hydrochloric acid (2.4 M, 250 ml.) was added to the above mixture. The resulting mixture was refluxed for 20 min and then allowed to stand at room temperature for 16 h. A precipitate formed and was collected by filtration. The solid was washed with water and dried to yield 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide (6.7 g,10 32 mmol, 44%)Data for 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide: MS (ESI) m/z: 209 ([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 4-Methoxy-3-methylphenylamine, its application will become more common.

Reference:
Patent; AKZO NOBEL N.V.; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/95014; (2006); A1;,
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14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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. 14869-41-1

27 mg, 0.34 mmol) of Intermediate 27a was added to 4 mL THF and stirred.Add 2-(2-chloro-ethoxy)acetic acid (48 mg, 0.34 mmol) and EEDQ (100 mg, 0.41 mmol), react at 60 ¡ã C for 4 hours, spin dry and add 5 mL of THF.NaH (40 mg, 1 mmol) was added portionwise with stirring, and reacted at room temperature for 5 hours.Add 0.2mL ammonium chloride solution, spin dry,The crude product was recrystallized from n-hexane andEtOAc to afford Intermediate 28z(174 mg, yield 76.0percent).

Statistics shows that 14869-41-1 is playing an increasingly important role. we look forward to future research findings about 2-(2-Chloroethoxy)acetic acid.

Reference:
Patent; Tianjin Pharmaceutical Institute Co., Ltd.; Wei Qunchao; Zheng Zhichao; Wang Songhui; Zheng Xuemin; Li Lingjun; Liu Lei; Yuan Jing; Zhang Shijun; Li Yuquan; Huang Changjiang; (38 pag.)CN109721539; (2019); A;,
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168971-68-4, The chemical industry reduces the impact on the environment during synthesis 168971-68-4, name is 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

Step 3: (1 -benzyl-3-(2-fluoro-4-(trifluoromethoxy)phenyl)-4-methyl-5-(trifluoromethyl)-1 H-pyrrol2-yl)(morpholino)methanone (SC-262)Under an nitrogen atmosphere (1 -benzyl-4-methyl-3-(4,4,5, 5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-5- (trifluoromethyl)-IH-pyrrol-2-yl)(morpholino)methanone (50 mg, 0.106 mmol) was dissolved in DMF (0.5 mL) and LiOH (2 mg, 0.106 mmol), bis(tri-tert-butylphosphine)palladium (0) (3 mg, 0.007 mmol) and 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene (24 mg, 0.096 mmol) were subsequently added. The reaction mixture was stirred at 80C under microwave irridation for I h. The mixture was cooled to RT and the reaction was stopped by addition of 1 M NaOH solution (2 mL). The crude product was extracted with EtOAc (2×3 mL) and the combined organic layers were washed with water (3×1 mL), dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude mass was purified by flash chromatography to give SC-262 (34 mg, 66.8 %).

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

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; WO2014/32801; (2014); A1;,
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2062-98-8, These common heterocyclic compound, 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, 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.

F[CF(CF3)CF2O]6CF(CF3)C(O)F, a precursor of hydrofluoroether F[CF(CF3)CF2O]7CH3, was formed by oligomerization of hexafluoropropylene oxide. To the reaction vessel, potassium fluoride (10.0 g), hexafluoropropylene oxide dimer (150.0 g) and tetraethylene glycol dimethyl ether (2.5 L) were added at 10 C under stirring.To the round bottom flask was introduced hexafluoropropylene oxide (830 g, 5.0 mol) over 1 hour.The lower acyl fluoride phase product is collected and consists mainly of hexafluoropropylene oxide oligomers. The crude product was further purified by distillation to obtain a product of a hexafluoropropylene oxide heptamer having a purity of 98% as determined by gas chromatography, and used in the next alkylation reaction. The structure of the product was characterized by infrared spectroscopy and 19F NMR.

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 2062-98-8.

Reference:
Patent; Tianjin Changlu Chemical New Materials Co., Ltd.; Yan Rui; He Guangrui; (15 pag.)CN109608312; (2019); A;,
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136-90-3,Some common heterocyclic compound, 136-90-3, name is 4-Methoxy-3-methylphenylamine, molecular formula is C8H11NO, 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.

EXAMPLE 134 2-[N-(4-Methoxy-3-methylphenyl)-carbamyloxymethyl]-norborn-5-en-2-yl methyl ketone 2.1 g of 80% strength NaH suspension are added to a solution of 10.54 g (0.77 mole) of 4-methoxy-3-methylaniline in 30 ml of THF and the mixture is heated to 40 C. to complete the elimination of hydrogen. When this has ceased, a solution of 20.0 g (0.77 mole) of (2-acetylnorborn-5-en-2-yl)-methyl phenyl carbonate in 20 ml of tetrahydrofuran is added dropwise at room temperature, and the mixture is then stirred for 18 hours at 20 C. After having added a small amount of water, the solvent is stripped off and the residue is taken up in ether. The ether phase is washed repeatedly with 5% strength sodium hydroxide solution, and with water, and is dried over sodium sulfate. The crystalline crude product (11.8 g) is recrystallized from ethyl acetate; 6.4 g of 2-[N-(4-methoxy-3-methylphenyl)-carbamyloxymethyl]-norborn-5-en-2-yl methyl ketone, of melting point 121-122 C., are obtained. Analysis calc. 69.28% C, 7.04% H, 4.25% N, 19.4% O: found 69.4% C, 6.9% H, 4.3% N: C19 H23 NO4 M.Wt. =329.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 136-90-3, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US4335138; (1982); A;,
Ether – Wikipedia,
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19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline, A new synthetic method of this compound is introduced below.

To a solution of 4-bromo-3-methoxyaniline (5.7 g, 28.2 mmol) in toluene (100 mL) and water (10 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-lH-pyrazole-l-carboxylate (9.96 g, 33.9 mmol), potassium phosphate (8.98 g, 42.3 mmol) and PdCl2(dppf)-DCM (1.152 g, 1.411 mmol) at RT. The reaction was stirred under argon at 95 ¡ãC for 2.5 hrs and then was cooled to RT. The reaction mixture was diluted with EtOAc, washed with H20, saturated aHC03 and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by normal phase chromatography to give Intermediate 1 as light tan solid (5.1 g, 63percent yield). LCMS (ESI) m/z: 290.1 (M+H)+; XH NMR (400MHz, chloroform-d) delta 8.35 (d, J=0.5 Hz, 1H), 8.01 (s, 1H), 7.29 (d, J=8.0 Hz, 1H), 6.37 – 6.26 (m, 2H), 3.84 (s, 3H), 3.79 (br. s., 2H), 1.66 (s, 9H).

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; BRISTOL-MYERS SQUIBB COMPANY; HU, Zilun; QUAN, Mimi L.; WO2014/134391; (2014); A1;,
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22236-10-8, The chemical industry reduces the impact on the environment during synthesis 22236-10-8, name is 4-(Difluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

Example 26 1- [(6-Aminopyridin-3-yl)methyl]-3-{[4-(diffuromethoxy)phenyl]amino}-4-phenyl- 1H-PYRROLE-2, 5-dione A mixture of tert-butyl {5- [ (3-chloro-2, 5-dioxo-4-phenyl-2, 5-dihydro-lH-pyrrol-l- yl) methyl]pyridin-2-yl} carbamate (0.70 g, 1.7 mmol) and 4- (difluoromethoxy)-aniline (0.54 g, 3.4 mmol) in DMF (4 mL) was heated in a microwave reactor at 150C for eight min.. The sovent was evaporated and the residue was purified on a column (ISOLUTE SI, LOG/70 mL), using CH2Cl2 and then CH30H/CH2C12 (1: 99,2 : 98 and then 5: 95) as eluant, to give 0.4 g (54%) of the title COMPOUND. 1H NMR (400 MHz, CDC13) 8 7.99 (bs, 1H), 7.67-7. 62 (m, 2H), 7.14-7. 04 (m, 3H), 6.91 (d, J =8 Hz, 2H), 6.78 (d, J=8 Hz, 1H), 6.72 (d, J=9 Hz, 2H), 6.63 (d, J=9 Hz, 2H), 6.33 (t, J=74 Hz, 1H), 4.60 (s, 2H).

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

Reference:
Patent; ASTRAZENECA AB; WO2005/5417; (2005); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., 22236-10-8

D. 7-(3-Chloropyridin-2-yl)-N-(4-(difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine A mixture of 4-chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (0.103 g, 0.000366 mol) and 4-(difluoromethoxy)aniline (0.091 mL, 0.00073 mol) in acetonitrile (3 mL, 0.06 mol) was heated via microwave in a sealed tube at 160 C. for 10 minutes. After cooling to room temperature, the mixture was added to saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Concentrated to leave an oil. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%) to give 0.113 g of a light yellow solid. MS: M+H=404 1H NMR (DMSO-d6): delta 2.80 (t, J=5.6 Hz, 2H); 3.68 (t, J=5.6 Hz, 2H); 4.35 (s, 2H); 7.04 (dd, J=7.6 Hz, 4,7 Hz, 1H); 7.15 (d, J=9.0 Hz, 2H); 7.17 (t, J=75.0 Hz, 1H); 7.69-7.74 (m, 2H); 7.86 (dd, J=7.9 Hz, 1.6 Hz, 1H); 8.24 (dd, J=4.7 Hz, 1.6 Hz, 1H); 8.40 (s, 1H); 8.57 (s, 1H).

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:
Patent; Kelly, Michael G.; Janagani, Satyanarayana; Wu, Guoxian; Kincaid, John; Lonergan, David; Fang, YunFeng; Wei, Zhi-Liang; US2005/277643; (2005); A1;,
Ether – Wikipedia,
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