Tag: M.W=200-300

These common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, 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. Quality Control of Methyl 2-(3-bromophenyl)acetate

Tributyltin methoxide (28.3 ml, 98 mmol), methyl (3-bromophenyl)acetate (WO 95/27692, pg. 16, e.g. 5a) (15.0 g, 65.0 mmol), isopropenyl acetate (10.8 ml, 98.0 mmol), palladium(II)acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 ml) at 100 C. under nitrogen for 5 hours. After cooling the reaction was diluted with ethyl acetate (150 ml) and 4M aqueous potassium fluoride solution (90 ml) and stirred for 15 minutes. The mixture was filtered through Arbocel and the organic phase separated and concentrated in vacuo. The residue was purified column chromatography on silica gel eluting with diethyl ether:pentane (0:100 to 25:75 and then changing to dichloromethane), to yield the title compound as a pale yellow oil, 12.6 g. 1HNMR(CDCl3, 400 MHz) delta: 2.15 (s, 3H), 3.61 (s, 2H), 3.69 (s, 5H), 7.10-7.13 (m, 2H), 7.19 (d, 1H), 7.30 (t, 1H) ppm. MS (electrospray): m/z 229 [MNa]+

The synthetic route of Methyl 2-(3-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brown, Alan Daniel; James, Kim; Lane, Charlotte Alice Louise; Moses, Ian Brian; Thomson, Nicholas Murray; US2005/171147; (2005); A1;,
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Related Products of 57486-69-8, 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. 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of aryl halide 4a (48 mg, 0.35 mmol) in 2 mL dimethylformamide were added boronic ester 5 (106 mg, 0.385 mmol), Pd(PPh3)4 (20 mg, 5 mol %), and K3PO4 (242 mg, 1.11 mmol). The mixture was irradiated at 150 C for 90 min using a microwave reactor. The reaction mixture was then diluted with EtOAc, filtrated on a small pad of Celite, and concentrated under vacuum. The crude mixture was then purified by column chromatography (DCM/CyHex 7/3) to afford 63 mg of the corresponding phenanthrene 7a (72% yield).

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-(2-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Rochais, Christophe; Yougnia, Rodrigue; Cailly, Thomas; Sopkova-De Oliveira Santos, Jana; Rault, Sylvain; Dallemagne, Patrick; Tetrahedron; vol. 67; 32; (2011); p. 5806 – 5810;,
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Synthetic Route of 1150566-27-0, 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. 1150566-27-0 name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, 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.

To 3,3,3-trifluoropropan-1-ol (19.9 mmol) in DMSO was added NaH (19.9 mmol). The mixture was allowed to stir at room temp under inert atmosphere for 1 h. Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (3.0 g, 13.3 mmol) was added and the reaction was warmed to 100 C until coupling was complete. After purification ethyl 6-(3,3,3-trifluoropropoxy)imidazo[1,2-b]pyridazine-3-carboxylate was obtained (1.2 g, 45%). MS (ESI) calcd for C12H12F3N3O3: 303.08

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GlaxoSmithKline LLC; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; (583 pag.)EP2768509; (2017); B1;,
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Reference of 99548-55-7, 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 99548-55-7 as follows.

Methyl 4-bromo-2-methylbenzoate (2.0 g, 8.73 mmol), cyclopropylboronicacid (1.1 g, 13.10 mmol), potassium phosphate (3.7 g, 17.46 mmol), tricyclohexylphosphine (0.245 g, 0.87 mmol) and palladium(II) acetate (0.195 g, 0.87 mmol) were combined in a sealed tube under nitrogen, then toluene (10 mL) and H20 (1 mL) was added in one portion. The reaction mixture was sealed and heated to 120°C for a period of 16 h. The reaction mixture was allowed to cool and diluted with EtOAc and washed with water. The organic extracts were washed with water and brine, dried and concentrated. The crude obtained was purified by column chromatography using 2-5 percent of EtOAc in hexane to afford the titled compound (1.3 g, 81 percent). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-dg) delta 7.72 (d, J=8.0 Hz, 1H), 7.01-6.97 (m, 2H), 3.78 (s, 3H), 2.50 (s, 3H), 1.92- 1.91 (m, 1H), 1.02-1.00 (m, 2H), 0.75-0.73 (m, 2H); LC/MS: 191 (Mu+1)+

According to the analysis of related databases, 99548-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; CHITTY VENKATA, Srikanth; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125408; (2014); A2;,
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Synthetic Route of 39149-80-9, The chemical industry reduces the impact on the environment during synthesis 39149-80-9, name is tert-Butyl 2-bromopropanoate, I believe this compound will play a more active role in future production and life.

To a solution of A-4 (200 mg, 0.68 mmol) in DMF (4 mL) was added tert-butyl 2-bromopropanoate (169.98 mg, 0.81 mmol) and CS2CO3 (441.45 mg, 1.35 mmol). The resulting mixture was stirred at 55 C for 2 hours. Saturated NH4C1 aqueous (20 mL) and EtOAc (20 mL) were added to the reaction mixture. After separation, the organic layer was washed with brine (20 mL x 2), dried over anhydrous Na2SC>4, filtered and concentrated to give the crude product that was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 10% to 20%) to afford A-51 (235 mg, 0.55 mmol) as an oil. 1H NMR (CDCI3, 400MHz) deltaH = 7.53 (d, 2H), 7.33 – 7.28 (m, 4H), 7.13 (s, 1H), 5.05 (q, 1H), 1.75 (d, 3H), 1.44 (s, 9H)

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, tert-Butyl 2-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
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Reference of 69812-51-7, 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. 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The reactions were carried out in a one-neck round bottomask. The corresponding 2-amino-2-methylpropanoic acid (0.88 g,8.5 mmol) and triethylamine (3.4 g, 34 mmol) were added to avigorously stirred mixture of water (5 mL) at 0C. When solidcompletely dissolved in water, 4-chlorosulfonyl benzoic acidmethyl ester (1 g, 4.3 mmol) was added dropwise over 30 min. Thenthe reaction was stirred at rt for 12 h, the product was extractedwith EtOAc (3 50 mL). Combined organic layers were dried overNa2SO4, concentrated in vacuo. The residue was puried by silicagel column chromatography (DCM/MeOH 30/1) to afford thedesired product. Yellow solid, m.p. 170.2e173.6C.1H NMR(400 MHz, DMSO) d 8.24 (s, 1H), 8.10 (d, J 8.4 Hz, 2H), 7.93 (d,J 8.4 Hz, 2H), 3.88 (s, 3H), 1.28 (s, 6H).13C NMR (100 MHz, DMSO)d 175.5, 165.7, 148.0, 132.9, 130.2, 127.0, 58.4, 53.0, 26.2. HRMS (ESI-TOF) m/z Calcd for C12H15NO6S [MNa]324.0518, found 324.0504.

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 4-chlorosulfonylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Wei; Xu, Xingyu; Zhao, Hongyan; Yan, Xiaoyu; Tetrahedron; vol. 74; 30; (2018); p. 4111 – 4118;,
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Adding a certain compound to certain chemical reactions, such as: 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, 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 15964-79-1, Computed Properties of C11H14O4

To a 250 mL three-necked flask, compound 6a (10 g, 0.048 mol) and 80 mL of tetrahydrofuran were added.Paraformaldehyde (15 g, 0.48 mol), potassium carbonate (20 g, 0.144 mol) were successively added, and reacted at 40 C. for 2 h.After the reaction was completed, the reaction solution was poured into a separatory funnel, 100 ml of water was added, and the mixture was extracted with 150 ml of tetrahydrofuran.The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness under reduced pressure to give 9.6 g of compound 5a.Yield 90.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(3,4-dimethoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang Yongning Pharmaceutical Co., Ltd.; Ye Tianjian; Lu Xiuwei; Yu Guangliang; He Si; (11 pag.)CN105153105; (2018); B;,
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Ester – an overview | ScienceDirect Topics

Application of 935273-86-2,Some common heterocyclic compound, 935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C12H12F2O2, 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 solution of benzyl 3,3-difluorocyclobutane carboxylate(450 mg, 2.0 mmol) dissolved in ethanol (10 mL), was added Pd/C(10%, 40 mg). The reaction mixture was stirred at room temperature for 10 hours under the atmosphere of hydrogen(15 psi). After TLC showed that the reaction was completed, the solid was filtered out, the filtrate was concentrated under vacuum to give 3,3-difluorocyclobutane carboxylic acid(250 mg, 83.1% yield) as a white solid. MS (ESI) Calcd. for C5H6F2O2 [M+H]+ 137, Found 137.

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

Reference:
Patent; Wuxi Fortune Pharmaceutical Co., Ltd; WU, Hao; LI, Peng; MAO, Weiwei; CHEN, Shuhui; WANG, Fei; LI, Jian; (53 pag.)EP3290418; (2018); A1;,
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Synthetic Route of 2876-78-0,Some common heterocyclic compound, 2876-78-0, name is Methyl 1-Naphthaleneacetate, molecular formula is C13H12O2, 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.

Triflic anhydride (16.6 mL, 0.099 mmol) and diphenyl sulfoxide (10.0 g, 49.4 mmol) and methyl 2- (naphthalen-l – yl) acetate (10.9 g, 54.5 mmol) in DCM (100 mL) solution of the It was added dropwise at -78 and stirred for 3 hours.Water was added (50 mL) quenched the reaction slowly, the mixture was slowly heated to room temperature.The layers were separated and the organic layer is required 2M sodium iodide solution (100 mL 10x), and water (3x 100 mL) was concentrated to a rear, viscous oil washed, precipitated the title compound which in MTBE (600 mL) ( 18.7 g, 74%) was obtained as a light brown hygroscopicsolid.

The synthetic route of 2876-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Rabom., Paul J.; (39 pag.)KR2015/35454; (2015); A;,
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Ester – an overview | ScienceDirect Topics

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. 26218-04-2, name is 2-Ethylhexyl 4-aminobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C15H23NO2

Cyanuryl chloride (18.4 g, 0.1 mol) is dissolved at 0 C.-5 C. in 150 ml of acetone in a reactor. Sodium bicarbonate (10.6 g, 0.1 mol) is added thereto and then a solution of 2-ethylhexyl para-aminobenzoate (24.9 g, 0.1 mol) dissolved in 150 ml of acetone is added dropwise at a temperature of less than 10 C. over 10 minutes. Subsequently, the heterogeneous mixture is left at laboratory temperature for 3 hours. 500 ml of water are run in. The precipitate formed is filtered off and then washed with water. After drying under vacuum, 38 g of an off-white solid are obtained. After recrystallizing this solid from 1,2-dichloroethane, 25.2 g (63% yield) of 2,4-dichloro-6-(2-ethylhexyl 4′-aminobenzoate)-s-triazine are obtained in the form of a white powder: UV (ethanol/DMSO): lambdamax=291 nm, E1%=732, which is used as is in the following stage.

According to the analysis of related databases, 26218-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; L’OREAL; US2007/196294; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics