Month: January 2021

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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-1,1-dimethoxyethane

Example 74; (IS, 2R) and (IR, 2S)-2-(4-chlorophenyl)-l’-(2-(4-isopropylpiperazin-l-yl)ethyl)spiro [cyclopropane-l,3′-indolin]-2′-oneSynthesis of (IR, 2S) and (IS, 2R)-2-(4-chlorophenyl)-l’-(2,2- dimethoxyethyl)spiro[cyclopropane-l,3′-indolin]-2′-one; To a solution of (IR, 2S) and (I S, 2R)-2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin]- 2′-one (135 mg, 1 mmol) in DMF (1 mL) was added KHMDS (0.5 M in THF, 1.1 mL) was dropwise at room temperature. The mixture was stirred for half an hour before adding bromoacetaldehyde dimethyl acetal (95 mg, 0.55 mmol). The mixture was warmed to 50 C and stirred at that temperature for 2 hours. The mixture was poured into water, extracted with ethyl acetate (3 x 15 mL), dried and concentrated under reduced pressure. Purification by flash column chromatography on silica gel, eluting with hexanes-EtOAc (6: 1 and then 4: 1) gave the desire product as colorless oil (268 mg, 75%). LC/MS m/e calcd. for C2oH2oClN03: 3570, observed (M+H)+: 358.7.

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; F. HOFFMANN-LA ROCHE AG; CHEN, Li; HUANG, Mengwei; FENG, Lichun; HE, Yun; YUN, Hongying; WO2011/69298; (2011); A1;,
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Electric Literature of 1535-75-7, These common heterocyclic compound, 1535-75-7, name is 2-(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.

General procedure: To a solution of respective anilines (1.0 eq.) in CH2Cl2 (15 mL) was added pyridine at 0 C and the mixture stirred for 5 min. Compound 4 (1.0 eq.) in CH2Cl2 (10 mL) wasadded and the mixture stirred at room temperature for 12-48 h. The mixture was diluted with CH2Cl2 (25 mL) and washed with diluted HCl and water. The organic layer wasdried over anhydrous Na2SO4 and concentrated to obtain crude was subjected to column chromatography on silica gel to yield title compounds 5.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abbavaram, Babul Reddy A.; Reddyvari, Hymavathi R.V.; Journal of the Korean Chemical Society; vol. 57; 6; (2013); p. 731 – 737;,
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Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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

According to route (C), 2-bromo-4-trifluoromethoxyaniline (2.3 mL, 15 mmoles, 1 eq.) was placed in l,4-dioxane (55 mL) with Pd(dppf)Cl2.CH2Cl2 (1.2 g, 1.5 mmole, 0.1 eq.). Upon addition of CS2CO3 (19.6 g, 60 mmoles, 4 eq.) and ethylboronic acid (3.3 g, 45 mmoles, 3 eq.), the reaction mixture was heated at l00C and stirred for 14 hours under an inert atmosphere of argon. The reaction mixture was then concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to afford 2-ethyl-4-(trifluoromethoxy)aniline (1.3 g, 42%). (0391) 6.93 (s, 1H), 6.90 (d, J = 8.5 Hz, 1H), 6.63 (d, J = 8.5 Hz, 1H), 3.64 (s, 2H), 2.49 (q, 7 = 7.5 Hz, 2H), 1.25 (t , J= 7.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 175278-17-8, its application will become more common.

Reference:
Patent; ABIVAX; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE MONTPELLIER; INSTITUT CURIE; SCHERRER, Didier; TAZI, Jamal; MAHUTEAU-BETZER, Florence; NAJMAN, Romain; SANTO, Julien; APOLIT, Cecile; (0 pag.)WO2020/11810; (2020); A1;,
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These common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, 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. Formula: C13H20O3

Step B: To the solution 3-azidopropoxyl beta-D-mannopyranoside (1030 mg, 3.91 mmol) in acetonitrile (15 ml) was added triethyl orthobenzoate (2.352 ml, 10.17 mmol) followed by TFA (0.030 ml, 0.391 mmol) and in ACN (0.5 mL). The mixture was allowed to stir at room temperature for 1 hour. Rotavap to remove ACN. TFA (10percent in water) (4.28 ml, 5.55 mmol) was added. The mixture was stirred at rt for 2 hours. The residue was purified by column chromatography on silica gel eluting with Ether/CH2Cl2 to give above product as a white solid. 1H NMR (CDCl3, 500 MHz): delta 7.0-8.2 (m, 10H), 5.72 (dd, 1H, J=3.4 Hz, J=1.1 Hz), 5.44 (t, 1H, J=9.6 Hz), 4.79 (d, 1H, J=1.1 Hz), 4.16 (dd, 1H, J=3.4 Hz, J=1.1 Hz), 4.00 (m, 1H), 3.88 (m, 1H), 3.82 (m, 1H), 3.66 (m, 2H), 3.31 (m, 2H), 1.82 (m, 2H).

The synthetic route of (Triethoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lin, Songnian; Yan, Lin; Kekec, Ahmet; Zhu, Yuping; Hunter, David N.; Huo, Pei; Feng, Danqing; Nargund, Ravi P.; Moyes, Christopher R.; Zhao, Zhiqiang; Pipik, Brenda; Pissarnitski, Dmitri; Duffy, Joseph L.; Guidry, Erin N.; US2015/105317; (2015); A1;,
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Reference of 20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Preparation of N-(2,4-dimethoxybenzyl)-6-fluoropyridin-2-amine To a mixture of (2,4-dimethoxyphenyl)methanamine (117.5 mL, 782.0 mmol) and N,N-diisopropylethylamine (147.6 mL, 847.2 mmol) in anhydrous dimethyl sulfoxide (500 mL) was added 2,6-difluoropyridine (75.0 g, 651.7 mmol). The resulting mixture was heated to 100 C. for 5 hours and then allowed to cool to ambient temperature. The mixture was diluted with ethyl acetate (600 mL), washed with water (1000 mL), saturated ammonium chloride (2*200 mL), brine (100 mL), and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo provided a residue, which was triturated in methanol (250 mL) to afford the title compound as a colorless solid (140.0 g, 82% yield): 1H NMR (300 MHz, CDCl3) delta 7.44 (q, J=8.2 Hz, 1H), 7.22 (d, J=8.2 Hz, 1H), 6.49 (d, J=2.3 Hz, 1H), 6.44 (dd, J=8.2, 2.4 Hz, 1H), 6.21 (dd, J=8.0, 2.4 Hz, 1H), 6.12 (dd, J=7.7, 2.3 Hz, 1H), 5.17-5.07 (m, 1H), 4.40 (d, J=6.0 Hz, 2H), 3.84 (s, 3H), 3.81 (s, 3H); MS (ES+) m/z 263.2 (M+1).

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, (2,4-Dimethoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xenon Pharmaceuticals Inc.; Andrez, Jean-Christophe; Burford, Kristen Nicole; Dehnhardt, Christoph Martin; Focken, Thilo; Grimwood, Michael Edward; Jia, Qi; Lofstrand, Verner Alexander; Wesolowski, Steven Sigmund; Wilson, Michael Scott; US2020/71313; (2020); A1;,
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Reference of 1535-73-5, The chemical industry reduces the impact on the environment during synthesis 1535-73-5, name is 3-Trifluoromethoxyaniline, I believe this compound will play a more active role in future production and life.

Add 3-(trifluoromethoxy)aniline (1.0 g, 5.65 mmol), pyridine (0.89 g, 11.3 mmol) to DCM (20 mL) and cool to 0 C. Add dropwise phenyl chloroformate (1.15 g, 7.34 mmol). After addition, stir for 1 hr. TLC (PE:EtOAc=3:1) shows the reaction is complete. Add water to the mixture, extract with DCM (10 mL*3), combine the organic layer, wash with 1N HCl solution, brine sequentially, and dry over anhydrous Na2SO4. Concentrate under reduced pressure to get the product (1.50 g, 89%). Intermediates D42-D46 can be synthesized with similar method (Table D9)

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, 3-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
Ether – Wikipedia,
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These common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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. Application In Synthesis of 2-(2-Methoxyphenoxy)ethylamine

General procedure: Corresponding 3-bromopropoxyaryl (5 mmol, 1 equiv) and amines(7.5 mmol, 1.5 equiv) was dissolved in 30 mL CH3CN. The reaction was purged with argon 3 times and stirred at reflux for 5 h, and then the mixture was cooled to room temperature and added AcOEt. Afte rwashing with brine 3 times, the organic layer was dried over anhydrous Na2SO4, filtered, and evaporated in vacuo. Purification of the crude residue by column chromatography on silica gel afforded target compounds.

The synthetic route of 2-(2-Methoxyphenoxy)ethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Qi; Chen, Zhuo; Hu, Gaoyun; Hu, Liqing; Li, Qianbin; Long, Jing; Bioorganic and medicinal chemistry; vol. 28; 9; (2020);,
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Application of 156573-09-0, These common heterocyclic compound, 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, 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.

Seventh Step: 1.76 g of well dried magnesium and 10 mL of THF were placed in a reactor under nitrogen atmosphere, and heated to 53 C. 17.2 g of the compound (1) dissolved in 30 mL of THF was slowly added dropwise thereto at a temperature range of from 50 to 56 C., followed by stirring for 30 minutes. Thereafter, 6.0 g of the compound (16) dissolved in 10 mL of THF was slowly added dropwise thereto at a temperature range of from 50 to 55 C., followed by stirring for 30 minutes. After cooling the resulting reaction mixture to 25 C., the reaction mixture was poured into and mixed with a mixture of 100 mL of 1N hydrochloric acid and 100 mL of toluene. The mixture was then separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution, and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain 18.5 g of 1-(4-ethoxy-2,3-difluorophenyl)-4-vinylcyclohexanol (17) as a yellow liquid.

The synthetic route of 156573-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHISSO Corporation; CHISSO PETROCHEMICAL Corporation; US2008/63814; (2008); A1;,
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Electric Literature of 446-59-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 446-59-3 name is 2-Bromo-1-fluoro-3-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 2-bromo-3-fluoroanisole (25 g), hexamethylenetetramine (34.2 g), and trifluoroacetic acid (150 mL) was stirred at 90C for 27 hours. The reaction mixture was allowed to cool to room temperature, and then 1 M hydrochloric acid was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, and then the organic layer was concentrated to about half of its volume. To the concentrated organic layer was added aqueous sodium hydroxide, and then the organic layer was separated from the mixture and washed with brine. The organic layer was dried over anhydrous sodium sulfate, and filtrated, and the solvent was removed. The obtained crude product was purified by silica gel column chromatography (heptane : ethyl acetate = 94 : 6 to 73 : 27) to afford the title compound as a white solid (22.3 g).1H-NMR (CDCl3) delta: 4.01 (3H, s), 6.82 (1H, d, J = 8.8 Hz), 7.85 (1H, dd, J = 8.8, 7.7 Hz), 10.22 (1H, d, J = 0.7 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-fluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KATOH, Takahiro; IIDA, Masatoshi; TERAUCHI, Yuki; YAMAGUCHI, Kazuya; HIROSE, Toshiyuki; YOKOYAMA, Fumiharu; NISHIMORI, Hikaru; OBUCHI, Yutaka; NABESHIMA, Hiroshi; TAKAKI, Emiri; (250 pag.)WO2017/150654; (2017); 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H5BrF3NO

Step 2: 5-methyl-2-(trifluoromethoxy) aniline 5-bromo-2-(trifluoromethoxy) aniline (1.14g, 4.46mmol) obtained from the last step, methyl boronic acid (0.72g, 12mmol), potassium carbonate (1.66g, 12mmmol), [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (0.29g, 0.4mmol) and 1,4-dioxane (25mL) were added to a 100mL reaction flask. The reaction mixture was heated up to 80 C and stirred overnight. After completion of the reaction, the reaction solution was concentrated and dissolved in ethyl acetate. The organic phase was washed with saturated ammonium chloride and saturated brine, dried, concentrated and purified by column chromatography (ethyl acetate/petroleum ether=1:15) to obtain the title compound (yellow oil, 0.61g, 72%). (MS: [M+1] 192.1)

The synthetic route of 886762-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Pearl Biotechnology Limited Liability Company; DONG, Jiaqiang; ZHONG, Boyu; YUAN, Hongbin; SHI, Quan; CHU, Shaosong; ZHANG, Deyi; ZHANG, Ruihao; (219 pag.)EP3150592; (2017); A1;,
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