Category: 14062-25-0

A common heterocyclic compound, 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, molecular formula is C10H11BrO2, 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. 14062-25-0.

Example 46A(+/-)-Ethyl (4-bromophenyl)(cyclopentyl)acetate; Under an atmosphere of argon, 5.54 g (49.4 mmol) of potassium tert-butoxide were dissolved in 100 ml of DMF, and the mixture was cooled to 0 C. 10 g (41.1 mmol) of ethyl 4-bromophenylacetate, dissolved in 20 ml of DMF, were then added. The reaction mixture was stirred at 0 C. for 30 min, and 5.29 ml (49.4 mmol) of cyclopentyl bromide were then added dropwise. The mixture was stirred at 0-5 C. for 1 h and then added to water (1 litre) and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. This gave 12.41 g (97% of theory) of the title compound in the form of a yellowish oil.LC-MS (Method 5): Rt=1.44 min; m/z=311/313 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.89-1.04 (m, 1H), 1.05-1.69 (m, 9H), 1.72-1.86 (m, 1H), 2.34-2.48 (m, 1H), 3.37 (d, 1H), 3.92-4.17 (m, 2H), 7.24-7.37 (m, 2H), 7.44-7.57 (m, 2H).

The synthetic route of Ethyl 2-(4-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-25-0, Name is Ethyl 2-(4-bromophenyl)acetate, 14062-25-0, 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.

Example 26; 2-(4-Bromo-phenyl)-acrylic acid ethyl esterTo a solution of (4-bromo-phenyl)-acetic acid ethyl ester (972.4 mg, 4 mmol), paraformaldehyde (240 mg, 8 mmol), and Bu4NCl (22 mg, 0.08 mmol) in DMF (10 mL) was added K2CO3 (1.32 g, 9.6 mmol). This mixture was heated at 60 degrees Celsius for 2 h. Then the mixture was cooled and diluted with EtOAc (30 mL) and washed with water (20 mL¡Á3), brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography on silica gel to give a white solid (0.74 g, 73%). MS: calc’d 255 (MH+), exp 255 (MH+).

Statistics shows that Ethyl 2-(4-bromophenyl)acetate is playing an increasingly important role. we look forward to future research findings about 14062-25-0.

Reference:
Patent; Liang, Chungen; Tang, Guozhi; Wong, Jason Christopher; Wu, Xihan; US2010/69328; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-25-0, 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 14062-25-0 as follows.

Ethyl-2-(4-bromophenyl)-2-diazoacetate (5j). To a solution of ethyl-4-bromophenylacetate (9j) (400 mg, 1.65 mmol) and 4-acetamidobenzenesulfonylazide (p-ABSA) (593 mg, 2.47 mmol) in dry CH3CN (4 mL) at 0C 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (376 mg, 2.47 mmol) was added. The mixture was stirred at it overnight, poured onto water (30 mL) andextracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine (40 mL), dried over Na2SO4 and the solvent evaporated under reduced pressure. The residue was dissolved in C112C12 (30 mL) whereby the side product 4-acetamidobenzenesulfonamide precipitated as a white solid. The suspension was filtered through silica gel and concentrated to afford an orange solid 5j (359 mg, 81 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 14062-25-0, and friends who are interested can also refer to it.

Reference:
Patent; ALLOCYTE PHARMACEUTICALS AG; BREITENSTEIN, Werner; HUERZELER, Marianne; KELLY, Terence; MANCUSO, Riccardo; SCHNEIDER, Gisbert; WEITZ-SCHMIDT, Gabriele; WO2015/189265; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, 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 14062-25-0. 14062-25-0

(4-bromophenyl)-acetic acid ethyl ester (0.1 g, 0.41 mmol) was dissolved in 1 mLof THF. t-BuOK (0.092 g,0.82 mmol) was added thereto, and iodomethane (0.051 mL, 0.82 mmol) was added thereto at 0C. The mixture wasstirred at room temperature for 18 hours. After addition of 1N HCl and water, the reaction solution was extracted withEtOAc. The organic layer was separated, dried with MgSO4 and purified by column chromatography to obtain the titlecompound (0.047 g, 42%).1H-NMR (CDCl3) delta 7.42 (2H, d), 7.21 (2H, d), 4.11 (2H, q), 1.54 (6H, s), 1.18 (3H, t).

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 Ethyl 2-(4-bromophenyl)acetate.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, I believe this compound will play a more active role in future production and life. 14062-25-0

Step a: Diethyl 2-(4-bromophenyl)malonate To a solution of ethyl 2-(4-bromophenyl)acetate (5.0 g, 21 mmol) in dry THF (40 mL) at -78 C. was added a 2.0M solution of lithium diisopropylamide in THF (11 mL, 22 mmol). After stirring for 30 minutes at -78 C., ethyl cyanoformate (2.0 mL, 21 mmol) was added and the mixture was allowed to warm to room temperature. After stirring for 48 h at room temperature, the mixture was quenched with water (10 mL). The reaction was partitioned between 1 N HCl (50 mL) and dichloromethane (50 mL), and the organic layer was separated. The organic layer was washed with 1 N HCl (50 mL), dried over Na2SO4 and evaporated. The crude material was purified by silica gel chromatography, eluding with 0-20% ethyl acetate in hexanes to give diethyl 2-(4-bromophenyl)malonate (2.6 g, 41%) 1H NMR (400 MHz, DMSO-d6) delta 7.60-7.58 (m, 2H), 7.36-7.34 (m, 2H), 5.03 (s, 1H), 4.21-4.09 (m, 4H), 1.20-1.16 (m, 6H).

The chemical industry reduces the impact on the environment during synthesis 14062-25-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hadida Ruah, Sara S.; Miller, Mark T.; Bear, Brian; McCartney, Jason; Grootenhuis, Peter D. J.; US2008/9524; (2008); A1;,
Ester – Wikipedia,
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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., 14062-25-0

Synthesis of compound 166.1. To a solution of ethyl 161.1 (5.0g, 20.6 mmol, l .Oeq) in CH2CI2 (50 mL) was added preraformaldehyde (0.938g, 24.69mmol, 1.2eq) followed by tetrabutylammonium chloride (0.571g, 2.05mmol, O. leq), and K2CO3 (6.2g, 45.26mmol, 2.2eq). The reaction was stirred at 60 C 3h. The reaction mixture was quenched with ice cold water and product was extracted with CH2CI2 (50mL x 2). Organic layer were combined and dried over sodium sulphate and concentrated under reduced pressure to obtain 166.1 (2.5g, 47.65%). MS (ES):256.4 m/z [M+H]+.

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; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-25-0, Adding some certain compound to certain chemical reactions, such as: 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, 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 14062-25-0.

Ethyl (4-bromophenyl)-acetate (100 g, 411 mmol) Z?-(pinacolato)diboron (125.4 g,493.7 mmol) and potassium acetate (125.4 g, 493.7 mmol) were charged to a 2 L round bottom flask. 1,4-Dioxane (1 L) was added and the mixture was stirred under a nitrogen EPO atmosphere for 15 minutes. [1,1 ‘-Z?w-(Diphenylphosphino)-ferrocene]dichloropalladium(II) CH2Cl2 complex (1:1) (3.36 g, 4.11 mmol) was added and the reaction was heated in an 100 0C oil bath for 2 hours. The reaction was determined complete by analytical HPLC. The solution was concentrated under reduced pressure to remove the dioxane and the residue was dissolved in ethyl acetate. The solution was filtered through a 6 x 4 inch silica gel plug with ethyl acetate (1.5 L) as eluant to give ethyl [4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- phenylj-acetate (117 g, 98%). 1H NMR (400 MHz, DMSO) delta ppm 7.63 (d, 2H5 J= 8 Hz), 7.27 (d, 2H, J= 8 Hz), 4.07 (q, 2H, J= 7 Hz), 3.68 (s, 2H), 1.28 (s, 12H), 1.16 (t, 3H, J= 7 Hz).

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 14062-25-0.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2006/86609; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics