Esters-buliding-blocks

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. 87-24-1, name is Ethyl 2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H12O2

Example 1 Preparation of intermediate A: Ethyl 2-methylbenzoate (15.0 g, 91 mmol) in ethyl acetate (400 mL) was treated with N-bromosuccinimide (19.5 g, 110 mmol). The resulting solution was illuminated with a 65 W mercury-halogen lamp for 16 h, which provided enough heat to bring the solution to a gentle reflux. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added (100 mL each). After separation of the organic layer, the aqueous layer was extracted with ethyl acetate (400 mL). The combined organic extracts were washed twice with water (100 mL each) and then with brine (100 mL), and then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product so obtained was purified by flash chromatography (ethyl acetate/hexane) to afford A as a yellow oil (21.3 g).

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 87-24-1.

Reference:
Patent; Roche Palo Alto LLC; US2010/16312; (2010); A1;,
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Electric Literature of 70347-04-5, 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. 70347-04-5, name is Methyl 4-methoxy-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-methoxy-3-methylbenzoate (16 g) was dissolved in EtOAc (100 mL) and then N- bromosuccinimide (18.96 g) and 2,2′-azobisisobutyronitrile (1 g) were added. The mixture was then heated to 800C for 4 h. After cooling to r.t. sat. sodium thiosulfate solution was added, the organic phase was separated, washed with brine, dried and the solvents removed by evaporation. The crude product was dissolved in mixture of isohexane-EtOAc (9:1) and a solid was produced which was collected to give the subtitle compound (11.82 g); 1H NMR (CDCl3): 8.05-7.98 (m, 2H), 6.91 (d, IH), 4.55 (s, 2H), 3.96 (s, 3H), 3.89 (s, 3H). LC-MS m/z 260.

The synthetic route of Methyl 4-methoxy-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; DAINIPPON SUMITOMO PHARMA CO., LTD; ASTRAZENECA UK LIMITED; BENNETT, Nicholas, James; MCINALLY, Thomas; THOM, Stephen; WO2010/133885; (2010); A1;,
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Some common heterocyclic compound, 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, molecular formula is C4H5ClF2O2, 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: esters-buliding-blocks

TEOF (130 g, 0.88 mol) was placed in a flask equipped with a magnetic stirring bar and a vacuum distillation cooler. ECDFAA (35 g, 0.175 mol) was added. The resulting mixture was heated to 110C (outer temperature of the flask) under a mild vacuum (300 mbar) ; ethanol formed during the reaction is slowly distilled out of the vessel. After 2h, the starting material was completely consumed, and product formation was observed by GC analysis. Excess of TEOF was removed from the reaction mixture by distillation (at 100C, starting with a pressure of 100 mbar at the beginning and 10 mbar at the end, to remove all TEOF traces), resulting pure product as pale yellow liquid with quantitative yield. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 1.15 (t, 3 H) 1.20 (t, 3 H) 1.27 (t, 3 H) 3.49 – 3.57 (m, 1H) 3.61 – 3.69 (m, 1H) 3.71 – 3.79 (m, 2 H) 4.23 (q, 2 H) 4.34 (d, J=8.24 Hz, 1 H) 5.18 (d, J=8.24 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 383-62-0, its application will become more common.

Reference:
Patent; SOLVAY SA; Januzems, Janis; EP2644598; (2013); A1;,
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Electric Literature of 18595-14-7, 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. 18595-14-7 name is Methyl 4-amino-3-methylbenzoate, 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.

Under a nitrogen atmosphere, to a 100-mL four-necked flask were added 5-methylmenthyl carboxylic acid (rac-11a) (600 mg, 3.03 mmol) obtained in Synthesis Example 7, 8, 9, or 19, thionyl chloride (0.33 mL, 1.50 eq.), and a catalytic amount of DMF, followed by stirring at room temperature for 3 hours. The solution in the system was distilled off under reduced pressure, and toluene (2 mL) was added thereto. The inside of the system was cooled to 10 C. or lower in an ice bath, and 3-methyl-4-aminobenzoic acid methyl ester (1.50 g, 3.0 eq.) was added slowly thereto. After two and a half hours, completion of the reaction was confirmed by GC-MS, and a post-treatment was performed. The reaction solution was transferred to a separating funnel, and tap water and chloroform were added thereto to effect washing. The oil layer was washed twice with dilute hydrochloric acid, and further washed once with a saturated saline solution, and then dried with anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and then isolation and purification were performed by column chromatography (heptane/ethyl acetate=4/1), whereby an amorphous solid was obtained (306 mg, yield: 29%). HRMS: mass: 345.2304 actual measurement value: 345.2298 1H-NMR (500 MHz, CDCl3): delta0.85-0.98 (m, 12H), 1.20-1.33 (m, 3H), 1.45-1.65 (m, 4H), 1.82 (quid, 1H, J=6.6, 2.1 Hz), 2.29-2.40 (m, 4H), 7.05 (br, 1H), 7.86-7.90 (m, 2H), 8.14 (d, 1H, J=8.2 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; TAKASAGO INTERNATIONAL CORPORATION; ITOH, Hisanori; HORI, Yoji; OTSUKA, Masashi; MATSUMOTO, Takaji; SATO, Tomoharu; (50 pag.)US2018/57447; (2018); A1;,
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Electric Literature of 91367-05-4, 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. 91367-05-4 name is Methyl 4-chloro-3-methylbenzoate, 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.

17.0 mL glacial acetic acid, 16.5 mL acetic anhydride and 2.5 mL H2SO4 were cooled in ice bath. Then X13 1.84 g (0.01 mol) and Cr2O3 3 g (0.03 mol) were added in small portion. The mixture was reacted in ice bath for 3 h. The reaction solution was poured into 200.0 mL ice water and stirred vigorously for 30 min. The resulting precipitates were collected by filtration and washed with water (70.0 mL x 3) to afford gray solid which was added into 50.0 mL eggplant flask. 16.0 mL CH3OH, 16.0 mL water and 0.4 mL H2SO4 were added to and refluxed for 30 min. The residue was added into water,and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined ethyl acetate extracts were washed with water (80 mL) and brine (80 mL) respectively, and then dried with anhydrous Na2SO4. When the solvent was evaporated, the yield of yellow solid compound X14 was 1.35 g (68.2 %). mp: 131-133 C. 1H NMR (300 MHz, DMSO-d6): delta 3.90 (s, 3H, OCH3), 7.79 (d, 1H, Ar-H, J = 8.4 Hz), 8.18 (d, 1H, Ar-H, J = 8.4 Hz), 8.35 (s, 1H, Ar-H), 10.34 (s, 1H, CHO). IR (KBr): 3425, 3082, 3003, 2953, 1726, 1720, 1689, 1188, 983, 759 cm-1. MS [M+H]+: 199.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-chloro-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Jiao, Yu; Xin, Bo-Tao; Zhang, Yanmin; Wu, Jianbing; Lu, Xiaolin; Zheng, Ying; Tang, Weifang; Zhou, Xiang; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 170 – 183;,
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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. 4519-46-4, name is Methyl 2-bromoacrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H5BrO2

(e) Methyl 2-[2-(Methyloxy)-8-quinolinyl]-2-propenoate To a solution of methyl 2-bromo-2-propenoate (452 mg, 2.74 mmol) (for a synthesis see Rachon, J.; Goedken, V.; Walborsky, H. J. Org. Chem. (1989), 54(5), 1006) in degassed tetrahydrofuran (10 ml) under an argon atmosphere was added [2-(methyloxy)-8-quinolinyl]boronic acid (506 mg, 2.49 mmol), bis(tri-t-butylphosphine)palladium (0) (25 mg, 0.05 mmol), bis(dibenzylideneacetone)palladium(0) (23 mg, 0.025 mmol) and potassium fluoride (477 mg, 8.217 mmol). The reaction was heated at 70 C. for 24 hours and then treated with water and dichloromethane. The aqueous fraction was re-extracted with dichloromethane. The combined organic fractions were then dried (MgSO4) and the solvent removed under reduced pressure. The residue was subjected to chromatography on silica gel using a ethyl acetate-hexane gradient. This provided the desired compound as a yellow solid (381 mg, 63%). MS (ES+) m/z 244 (MH+, 100%), 212 (80%).

The synthetic route of 4519-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cailleau, Nathalie; Davies, David Thomas; Esken, Joel Michael; Hennessy, Alan Joseph; Kusalakumari Sukumar, Senthil Kumar; Markwell, Roger Edward; Miles, Timothy James; Pearson, Neil David; US2008/221110; (2008); A1;,
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Related Products of 135908-33-7, These common heterocyclic compound, 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 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: Example 69: 4-(((6-((trans-4-(tert-butyl)cyclohexyl)oxy)quinolin-2-yl)methyl)amino)bicyclo[2.2.2] octane-l-carboxylic acid Step 1: methyl 4-(((6-((trans-4-(tert-butyl cyclohexyl oxy quinolin-2-yl methyl amino bicyclor2.2.21oct ane- 1 -carboxylate 2) NaBH(OAc)3 (3 eq), it, 1 h Y: 30% The solution of 6-((trans-4-(tert-butyl)cyclohexyl)oxy)quinoline-2-carbaldehyde (200 mg, 0.6 mmol) and methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (142 mg, 0.644 mmol) in Ethanol (2 mL, 30 mmol) was heated to reflux for 2h. The yellow solution was cooled to room temperature and sodium cyanoborohydride (48.6 mg, 0.773 mmol) was added and was heated to reflux for lh. After cooled down to room temperature, citric acid was added and concentrated down. The solid was suspended in water and filtrate, and the collected solid was washed thoroughly with water. HPLC purification of the solid give the product (62.7 mg, 20%). LCMS Rt = 1.67 min, m/z = 479.30 [M+l]. Lithium hydroxide (15.7 mg, 0.655 mmol) was added to a solution of 4-{ [6-(trans-4-tert-Butyl-cyclohexyloxy)-quinolin-2-ylmethyl]-amino}-bicyclo[2.2.2]octa ne-l-carboxylic acid methyl ester (62.7 mg, 0.131 mmol) in tetrahydrofuran (0.8 mL, 10 mmol) and methanol (0.8 mL, 20 mmol). The mixture was stirred at 50 C overnight, the solvent was concentrated. The residue was taken up in DMSO and cone. HCl (200 uL) was added to solubilize. Purification by preparative HPLC gave the product as a white solid (63 mg, 20%). LCMS (100%, RT=1.57 min, m/z=465.30. 1H NMR (400 MHz, METHANOL-d4) delta ppm 0.94 (s, 9 H) 1.06 – 1.60 (m, 5 H), 1.86 – 1.99 (m, 2H), 2.00- 2.10 (m, 12 H), 2.24 – 2.37 (m, 2 H) 4.32 – 4.46 (m, 1 H) 4.49 (s, 2 H) 7.34 (d, J=2.51 Hz, 1 H) 7.42 (dd, J=9.29, 2.76 Hz, 1 H), 7.47 (d, J=8.53 Hz, 1 H) 8.01 (d, J=9.29 Hz, 1 H) 8.28 (d, J=8.28 Hz, 1 H). Step 2: 4-(((6-((trans-4-(tert-butyl)cvclohexyl)oxy)quinolin-2-yl)methyl)amino)bicyclor2.2.21oct ane-l-carboxylic acid Lithium hydroxide (15.7 mg, 0.655 mmol) was added to a solution of 4-{ [6-(trans-4-tert-butyl-cyclohexyloxy)-quinolin-2-ylmethyl]-amino}-bicyclo[2.2.2]octa ne-l-carboxylic acid methyl ester (62.7 mg, 0.131 mmol) in tetrahydrofuran (0.8 mL, 10 mmol) and methanol (0.8 mL, 20 mmol). The mixture was stirred at 50 C overnight, the solvent was concentrated. The residue was taken up in DMSO and cone. HCl (200 uL) was added to solubilize. Purification by preparative HPLC gave the product as a white solid (2.3 mg, 4%). LCMS (100%, RT=1.57 min, m/z=465.30. 1H NMR (400 MHz, METHANOL-d4) delta ppm 0.94 (s, 9 H) 1.06 – 1.60 (m, 5 H), 1.86 – 1.99 (m, 2H), 2.00- 2.10 (m, 12 H), 2.24 – 2.37 (m, 2 H) 4.32 – 4.46 (m, 1 H) 4.49 (s, 2 H) 7.34 (d, J=2.51 Hz, 1 H) 7.42 (dd, J=9.29, 2.76 Hz, 1 H), 7.47 (d, J=8.53 Hz, 1 H) 8.01 (d, J=9.29 Hz, 1 H) 8.28 (d, J=8.28 Hz, 1 H).

Statistics shows that Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 135908-33-7.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; MI, Sha; PENG, Hairuo; SHAO, Zhaohui; SUN, Lihong; TAVERAS, Arthur; XIN, Zhili; ZHANG, Lei; WO2014/18891; (2014); A1;,
Ester – Wikipedia,
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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. 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 35418-07-6

Methyl 4-[N,N-bis(2-hydroxyethyl)amino]phenylpropionate Methyl 3-(4-aminophenyl)propionate (4.3 g; 24 mmol) was reacted with 11 g (250 mmol, 10 equivalents) of ethylene oxide in 24 ml of 30% acetic acid in a similar manner to Reaction 3 in Example 21. The reaction mixture was worked up. The crude product so obtained was purified by chromatography on a silica gel column (methylene chloride/2-4% methanol) and then crystallized from n-hexane-ethyl ether, whereby 5.04 g (18.9 mmol) of the title compound were obtained as white crystals (yield: 78.6%).

According to the analysis of related databases, 35418-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; US5852011; (1998); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 57486-68-7, 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. 57486-68-7, name is Methyl 2-chlorophenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dark red solution of (2-chlorophenyl)acetic acid methyl ester (TCI, 1.53 mL, 10.0 mmol), NIS (2.36 g, 10.5 mmol) and AuCl3 (152 mg, 0.50 mmol) in DCE (25 mL) was stirred at reflux under Ar for 18 h. The solution was cooled to RT, NIS (563 mg, 2.50 mmol) added and the purple solution stirred at reflux for 2 h. The solution was cooled to RT, filtered through Celite and the filtercake washed with DCM. The combined organics were concentrated in vacuo to leave a solid that was dissolved in diethyl ether (50 mL), washed with water (2 x 50 mL), brine (50 mL), dried (Na2S04), filtered and concentrated in vacuo to leave a purple oil (3.0 g). FCC, using 2-7% EtOAc in cyclohexane, gave the title compound as a clear oil (1.07 g, 34%) and a clear oil (mixed fractions, 814 mg, 26%). LCMS (Method 3): Rt 4.09 min, m/z 311 [MH+].

The synthetic route of Methyl 2-chlorophenylacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); A1;,
Ester – Wikipedia,
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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 56741-34-5 as follows. HPLC of Formula: C8H8FNO2

[00326] To a stirred solution of methyl 5-amino-2-fluorobenzoate (500 mg, 2.99 mmol) in DCM (20 mL) at 0 C, was added 3,4-difluorobenzoyl chloride (410 mu, 3.26 mmol) followed by TEA (1.0 mL, 7.48 mmol). The mixture was allowed to warm to rt and stirred for 72 h. The mixture was diluted with water and the organic layer separated and concentrated under reduced pressure. The obtained solid was purified via trituration with Et20 to afford compound 1 (782 mg, 84%) as a white solid. 1H MR (400 MHz, DMSO-i): delta 10.53 (s, 1H), 8.35 (m, 1H), 8.00 – 8.10 (m, 2H), 7.88 (m, 1H), 7.66 (m, 1H), 7.38 (m, 1H), 3.85 (s, 3H); LCMS Mass: 310.0 (M++l).

According to the analysis of related databases, 56741-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; (183 pag.)WO2018/183122; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics