Category: 24393-53-1

Adding a certain compound to certain chemical reactions, such as: 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, 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 24393-53-1, category: esters-buliding-blocks

Example 1; 4′-((1S.2SV2-ir(2S)-2-MethylPyrrolidin-1-v?methyllcvcloproDvn-1.1′-biphenyl-4- carbonitrile; Example 1A; fra/7S-3-(4-Bromophenyl) prop-2-en-1 -ol; To a solution of ethyl trans-4-bromocinnamate (8 ml_, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C dropwise. After the addition, the mixture was allowed to warm from -78 0C to -30 0C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added till acidic (pH=2). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried withMgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz1 1H)1 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz, J =3 Hz, 1H), 7.25 (d, J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.; Example 26; 4′-(f1R.2S)-2-(2-ff2R)-2-Methylpyrrolidin-1-yl1ethyl>cvclopropyh-1.1′-biphenyl-4- carbonitrile; Example 26A; 3-(4-BromophenvQprop-2-ene i-p|; To a solution of ethyl trans-4-bromocinnamate [CAS 24393-53-1] (8 mL, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added dropwise diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C. Following the addition, the mixture was allowed to warm from -780C to -300C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added. The organic layer was separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz, 1 H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt. J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz1 J =3 Hz, 1H), 7.25 (d. J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H); Example 34; 2-r4-((1S.2S)-2-(f(2S)-2-MethylPyrrolidin-1-yllmethyl)cvclopropyhphenyllPyridazin- 3(2H)-one; Example 34A; (E)-3-(4-bromophenyl)prop-2-en-1-ol; To a solution of (E)-ethyl 3-(4-bromophenyl)acrylate (25 g, 96 mmol) inDCM (300 ml) under nitrogen and cooled to -78 0C was added dropwise DIBAL-H (240 ml, 1 M in DCM, 240 mmol) in about 20 minutes. The mixture was stirred at -780C for 2 hours. Then, the dry ice bath was removed. The reaction was diluted with DCM (500 ml_), quenched with HCI (1N), and partitioned. The combined organic phases were washed with HzO, dried and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.43 (t, J = 6 Hz1 1H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz, 1H), 6.57 (d, J =15 Hz, 1H), 7.25 (d, J = 9 Hz, 2H)1 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; WO2007/150010; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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.

308 mg (0.26 mmol, 5 mol%) of tetrakis(triphenylphosphine)palladium are added to a solution of 2 g (5.34 mmol, 1.0 eq) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]urea and 1.6 g (6.4 mmol, 1.2 eq) of ethyl 4-bromocinnamate in 20 mL of an 8/2 mixture of dimethylformamide and of 2M potassium phosphate solution. The reaction mixture is stirred for 3 hours at 90C. The reaction is stopped by addition of 50 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.69 g of ethyl 3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylate in oil form are obtained. Yield = 75 %

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 3-(4-bromophenyl)acrylate, its application will become more common.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18326; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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.

30 mg (0.02 mmol, 5 mol%) ofpalladiumtetrakis(triphenylphosphine) are added to a solution of 200 mg (0.53 mmol, 1.0 eq.) of methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]octanamide and 204 mg (0.80 mmol, 1.5 eq.) of ethyl 4-bromocinnamate in 3 ml of a mixture of dimethylformamide and of a 2M potassium phosphate solution (6/1). The reaction mixture is stirred at 80C for 2 hours. The reaction is halted by the addition of 5 ml of water and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulphate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 145 mg of ethyl 3-(3′-[((methyl)(octanoyl)amino)methyl]biphenyl-4-yl}acrylate are obtained in the form of an oil. Yield = 63%

The synthetic route of 24393-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18325; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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 a solution of (£ ethyl 3-(4-bromophenyl)acrylate (10.0 g, 39.2 mmol) in THF (150 mL) was slowly added at -78 C a solution of DIBA1-H (86 mL of 1M solution in hexanes, 86.0 mmol). The resulting solution was then allowed to slowly warm to 0 C, after which a further 10 mL of DIBA1-H solution was added. TLC analysis indicated complete reaction and the mixture was re-cooled to -78 C. MeOH was then slowly added to quench the remaining reducing agent and the mixture allowed to warm back to rt over 30 minutes. The resulting mixture was poured into a saturated aqueous solution of Rochelle’s salt and then extracted with EtOAc. The organic phase was separated, dried (MgSO i), filtered and the filtrateconcentrated in vacuo. The crude product thus obtained was purified on silica eluting with a gradient of 0 to 35% EtOAc in hexanes to afford 6.0 g (71%) of (£)-3-(4-bromophenyl)prop-2-en-l-ol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 3-(4-bromophenyl)acrylate, its application will become more common.

Reference:
Patent; INCEPTION 2, INC.; STOCK, Nicholas, Simon; CHEN, Austin, Chih-Yu; BRAVO, Yalda, Mostofi; JACINTHO, Jason, Duarte; SCOTT, Jill, Melissa; STEARNS, Brian, Andrew; CLARK, Ryan, Christopher; TRUONG, Yen, Pham; WO2013/134562; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 24393-53-1, 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. 24393-53-1 name is (E)-Ethyl 3-(4-bromophenyl)acrylate, 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 method for constructing a quaternary carbon ring by visible light catalysis [2+2] reaction, comprising the following steps: The ruthenium complex 1 is used as a visible light catalyst, and 1.3 mg of the catalyst is added to 2 mL of 1,2-dichloroethane.0.2 mmol of (E)-ethyl-3-p-bromophenyl acrylate (corresponding R2 is p-bromophenyl, R3 is ethoxy), 1.0 mmol of 1,1-diphenylethylene (corresponding R1 is benzene) The base, R2 is a phenyl group) wherein the concentration of the visible light catalyst is 1.0 x 10-3 M. Pass argon for ten minutes,Then, with 450 nm ± 10 nm Blue LEDs, the light was illuminated in an argon atmosphere at 25 C for 5 h.After the reaction is completed, it is directly dried and separated by a column. Nuclear magnetic resonance spectrum, carbon spectrum,Mass spectrometryThe compound is a racemic ethyl-(2R)-2-(p-bromophenyl)-3,3-diphenyl-cyclobutyl-1-carboxylate.The conversion of the starting material was 100% and the yield of the cyclobutane product was 85%.

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

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Wu Lizhu; Lei Tao; Zhao Leimin; Zhou Chao; Liu Zan; Tong Zhenhe; (89 pag.)CN108623425; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics