Category: esters-buliding-blocks

1117-71-1, name is Methyl 4-bromobut-2-enoate, belongs to esters-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. Quality Control of Methyl 4-bromobut-2-enoate

To the suspension of potassium phthalimide (4.5 mmol) in dry DMF (4 mL) was added a solution of (E)-alkyl -bromobut-2-enoate in dry DMF (3 mL). The reaction was run at room temperature overnight. After the reaction was omplete, the reaction mixture was poured into water and extracted with ether and concentrated in vacuum to leave a hite solid. The residue can be easily purified by flash chromatography (petroleum/ethyl acetate, 4:1), to give the desired compounds 1.

The synthetic route of 1117-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fuzhong; Chen, Jun; Zhang, Xiangyang; Liu, Jibing; Cun, Linfeng; Zhu, Jin; Deng, Jingen; Liao, Jian; Tetrahedron Letters; vol. 52; 7; (2011); p. 830 – 833;,
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Electric Literature of 346603-63-2, The chemical industry reduces the impact on the environment during synthesis 346603-63-2, name is Methyl 2-methyl-3-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

To a solution of 2-methyl-3-trifluoromethyl-benzoic acid methyl ester (0.95 g, 4.35 mmol) in benzene (10 mL) was added N-bromosuccinimide (0.77 g, 4.33 g) and benzoyl peroxide (0.052 g, 0.21 mmol) and the resulting mixture heated to reflux for 4 h, cooled and stirred at room temperature for 48 h. The mixture was filtered, the filter cake washed with diethyl ether and the filtrate washed with a 1 N sodium thiosulfate solution (10 mL), brine and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue purified via automated flash chromatography (Analogix, SF25-80 g column, 5->10% ethyl acetate/hexane gradient) to give 2-bromomethyl-3-trifluoromethyl-benzoic acid methyl ester (1.04 g, 3.50 mmol, 81%) as an off white solid; 1H NMR (300 MHz, DMSO-d6) delta ppm 3.72-4.16 (m, 3H), 5.03 (s, 2H), 7.47-8.32 (m, 3H).

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, Methyl 2-methyl-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Orzechowski, Lucja; US2012/283271; (2012); A1;,
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Application of 2555-28-4, 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. 2555-28-4, name is 7-Methoxy-4-methylcoumarin belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N-Bromosuccinimide (224 mg, 1.26 mmol) was added slowly to a suspension of 7-methoxy-4-methyl-2H-chromen-2-one (17) (200 mg, 1.05 mmol) in PEG-400 (6 mL). The reaction mixture was stirred at rt for 2 h. The reaction mixture was extracted with H2O (25 mL) and EtOAc (3 * 25 mL) and the combined organic phases were washed with brine (30 mL). The organic phase was dried over Na2SO4. After concentration in vacuo the crude product was purified by column chromatography on silica gel. This afforded the titled compound as a white solid (130 mg, 0.48 mmol, 46% yield); Rf = 0.35 (EtOAc/heptane 1:2); mp 144-146 C (decomposed); 1H NMR (300 MHz, CDCl3) delta 2.60 (s, 3H), 3.88 (s, 3H), 6.81 (d, J = 2.7 Hz, 1H), 6.88 (dd, J = 9.0, 2.7 Hz, 1H), 7.54 (d, J = 9.0 Hz, 1H); 13C NMR (75 MHz, CDCl3) delta 19.5, 55.8, 100.7, 109.7, 112.9, 113.4, 126.0, 151.1, 153.6, 157.3, 162.7; LC-MS [M+H]+ calcd for C11H9BrO3: 269.0, found: 269.0; Anal. calcd for C11H9BrO3: C, 49.10, H, 3.37, found: C, 48.76; H, 3.13.

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, 7-Methoxy-4-methylcoumarin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Huynh, Tri H.V.; Abrahamsen, Bjarke; Madsen, Karsten K.; Gonzalez-Franquesa, Alba; Jensen, Anders A.; Bunch, Lennart; Bioorganic and Medicinal Chemistry; vol. 20; 23; (2012); p. 6831 – 6839;,
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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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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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. 19878-18-3, name is trans-Ethyl 4-(aminomethyl)cyclohexanecarboxylate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H20ClNO2

To a mixture of trans-4-(aminomethyl)cyclohexaneethylcarboxylate hydrochloride (3.00 g, 13.5 mmol) prepared as above and K2CO3 (3.73 g, 27.1 mmol) in CH3CN (100 mL) at 09C was added a solution of bromoacetyl bromide (1.1 mol equiv in 20 mL of CH3CN) slowly over 1 h. After 18 h of stirring at 80 C., the inorganic salts were removed by filtration and the organic phase was evaporated under reduced pressure. The residue was washed with H2O (30 mL¡Á3 times) and dissolved in CH2Cl2. The organic phase was dried over Na2SO4, filtered, and evaporated to give a crude product which was further purified by chromatography on silica [gradient elution CH2Cl2 to 30% ethyl acetate (EA)-CH2Cl2, Rf=0.5 (EA/CH2Cl2=4:6)] to obtain ethyl 4-((2-bromoacetamido)methyl)cyclohexanecarboxylate as a white solid. Yield: 2.49 g (60%). 1H NMR (CDCl3): delta=6.54 (br, 1H, -CONH-), 4.12 (q, 2H, -OCH2CH3), 3.90 (s, 2H, BrCH2CO-), 3.16 (t, 2H, -CONHCH2-), 2.22 (m, 1H, CH3CH2COOCH-, cyclohexyl), 1.80-2.10 (m, 4H, CH2-, cyclohexyl), 1.52 (m, 1H, NHCH2CH-, cyclohexyl), 1.49-1.37 (m, 2H, -CH2-, cyclohexyl), 1.24 (t, 3H, -COOCH2CH3), 1.08-0.92 (m, 2H, -CH2-, cyclohexyl). 13CNMR (CDCl3): delta=175.79 (BrCH2 CONH-), 165.57 (-COOCH2CH3), 60.23 (-COOCH2CH3), 45.96 (-COOCH-, cyclohexyl), 43.17 (-NHCH2CH-), 37.12 (-NHCH2 CH-, cyclohexyl), 29.68 (BrCH2CO-), 29.35 (-CH2-, cyclohexyl), 28.34 (-CH2-, cyclohexyl), 14.22 (-COOCH2 CH3). Anal. Calc. for C12H20BrNO3: C, 47.07; H, 6.58; N, 4.57. Found: C, 47.78; H, 6.85; N, 4.72 (purity>95%). FAB-MS (m/z): Calc. for C12H21BrNO3, 306.07 ([MH]+). Found: 306.20.

According to the analysis of related databases, 19878-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYUNGPOOK NATIONAL UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; Kim, Tae-Jeong; Chang, Yong Min; Kim, Hee-Kyung; Gu, Sung-Wook; US2013/231475; (2013); A1;,
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Application of 33689-29-1, 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. 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : methyl 1-(5-bromo-4-fluoro-2-nitrophenoxy)cvclopropanecarboxylate: To a mixture of methyl 1-hydroxycyclopropanecarboxylate (Aldrich) (1.0 g, 8.8 mmol) and 15- crown-5 (cat. amount) in THF (30 ml) was added NaH (400 mg, 10 mmol) at room temperature. The resulting mixture was stirred at room temperature for 30 min and then added 1-bromo-2,5- difluoro-4-nitrobenzene (Aldrich) (2 g, 8.4 mmol). The mixture was stirred at room temperature for additional 16 hrs. When TLC indicated the reaction was completed, the reaction mixture was quenched with saturated NH4CI aqueous solution. After removal of the organic solvent, the mixture was extracted with ethyl acetate (x3). The combined organic phases were washed with brine (x3), dried over anhydrous Magnesium sulfate and filtered. The filtration was concentrated under reduced pressure to give the crude product, which was purified by flash column chromatography on silica gel using a gradient 0-10% ethyl acetate in hexanes to afford the title compound as yellow solid. LC-MS: Rt=1.43 mins; MS m/z [M+H]+ 333.9; Method 5-95AB 1.5minLC_v003 1H NMR (400 MHz, CDCI3) delta 8.15 (1 H, d), 6.98 (1 H, d), 3.57 (3H, s), 1.38 (2H, m), 1.18 (2H, m).

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

Reference:
Patent; NOVARTIS AG; CHEN, Shuhui; HE, Haiying; LAGU, Bharat; QIN, Hua; WU, Chengde; XIAO, Yisong; WO2015/102929; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35179-98-7, name is Chloromethyl ethyl carbonate, belongs to esters-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 35179-98-7, Product Details of 35179-98-7

To a 100 ml of one-necked flask, 0.698 g of material, 0.162 g of potassium carbonate, 5 ml of N,N-dimethylacetamide were added in turn. The solution was stirred at room temperature for 20 minutes. Then 0.702 g of chloromethyl ethyl carbonate was added and the mixture was reacted at 45-50 C. for 16 hours. After the reaction was completed, the mixture solution was filtered, and 30 ml of water was added into the filtrate. The resulting mixture was extracted with 30 ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.854 g of oil, which was directly used in the next reaction without purification.10 ml of dioxane and 5 ml of 4 mol/L HCl were added and the resulting mixture was reacted at room temperature for 16 hours. The reaction was stopped and the solution was adjusted to pH 6-7 using aqueous sodium bicarbonate solution. The solution went turbid, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, concentrated to give 0.420 g of 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 1-[(ethoxycarbonyl)oxy]methyl ester.1H-NMR (CDCl3) delta H (ppm) 0.92 (t, 3H, J=17.5), 1.23 (t, 3H, J=14.0), 1.37 (m, 2H, J=34.2), 1.73 (m, 2H, J=30.8), 2.69 (t, 2H, J=15.5), 4.13 (q, 2H, J=15.7), 5.58 (s, 2H), 5.89 (s, 2H), 6.99-7.61 (8H), 8.16 (d, 1H, J=6.1)ESI(-): 539.1Mp: 164.5-160 C.

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, Chloromethyl ethyl carbonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guo, Jianhui; An, Dong; US2009/36505; (2009); A1;,
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Synthetic Route of 89-91-8, 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 89-91-8 as follows.

To a solution of lithium aluminium hydride (3.4 g) in tetrahydrofuran (150 mL) was added dropwise a solution of methyl dimethoxyacetate (9.83 mL) in tetrahydrofuran (50 mL) under ice-cooling, and the mixture was stirred at 0 C. for 3 hr. To the reaction mixture was added sodium sulfate decahydrate (45 g) at 0 C., and the mixture was filtered through Celite. The solvent was evaporated under reduced pressure to give the title compound (5.45 g). 1H NMR (300 MHz, DMSO-d6) delta 3.27 (6H, s), 3.32-3.37 (2H, m), 4.29 (1H, t, J=5.5 Hz), 4.69 (1H, t, J=6.1 Hz).

According to the analysis of related databases, 89-91-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); 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. 27798-60-3, name is Methyl 2-Methoxyphenylacetate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H12O3

(b) Sodium (590 mg) was dissolved in ethanol (45 mL) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.65 g, 12 mmol), followed by methyl 2-methoxyphenylacetate (4.7 g, 26 mmol) were added. The reaction mixture was refluxed overnight, the solvent was stripped and the residue was treated with water and then 2N HCl. The product was collected by filtration and recrystallized from ethyl acetate to afford 2.23 g of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 145-146 C.

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 27798-60-3.

Reference:
Patent; Sanofi Winthrop, Inc.; US5656629; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 13671-00-6, name is Methyl 2,6-difluorobenzoate, belongs to esters-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 13671-00-6, name: Methyl 2,6-difluorobenzoate

Fuming nitric acid (1 1 g, 174 mmol) was added to a solution of methyl 2,6- difluorobenzoate (25 g, 145 mmol) in concentrated sulfuric acid (50 ml_) at 0 C, and the reaction was stirred for 30 min at 0C. The reaction mixture was poured over ice-water. The precipitate was filtered to give the title compound 25.1 g (80.6 % yield) 1H NMR (400 MHz, CDCI3) delta ppm 8.13-8.20 (m, 1 H), 7.02-7.10 (m, 1 H), 3.93 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,6-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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