Category: 3650-78-0

Related Products of 3650-78-0,Some common heterocyclic compound, 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate, molecular formula is C10H9BrO2, 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.

Compound (7.5 g) obtained from step a above, pyridine-2-methoxy-5-boronic acid (9.48 g), tetrakistriphenylphosphinepalladium (0) (1.79 g) and potassium carbonate (12.83 g) were taken in dimethylformamide (60 mL) under nitrogen atmosphere. The reaction mixture was refluxed under nitrogen atmosphere for 6 hours. After cooling to room temperature, water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and the solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash column chromatography using 20-30 % ethyl acetate in hexane to get the title compound (8.09 g).

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

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2008/23336; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 3650-78-0, 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. 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)-3-oxo hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylic acid tert-butyl ester (1.80 g, 7.46 mmol),Methyl 4-bromocinnamate (2.0 g, 8.3 mmol),Palladium acetate (84 mg, 0.37 mmol),2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (320 mg, 0.75 mmol) andCesium carbonate (3.65g, 11.2mmol)Soluble in 1,4-dioxane (20 mL),The reaction was stirred at 100 C for 12 h under a nitrogen atmosphere.Cool to room temperature, filter, filter cake washed with dichloromethane (100 mL),The residue was purified by silica gel column chromatography (PE/EA (V/V)=3/1).The title compound was obtained as a white solid (1.95 g, 65.1%).

The synthetic route of Methyl 3-(4-bromophenyl)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ·geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 3650-78-0 as follows. category: esters-buliding-blocks

To a stirred solution of benzyl bromide (27 mL, 227 mmol) in acetone at r.t. was added tetrahydrothiophene (10.0 mL, 1 14 mmol). The solution was stirred for 16 h and the resulting precipitate filtered and washed with acetone (3 x 50 mL) and dried under air, to give 1 -benzyltetrahydrothiophenium bromide as a white solid (51 .9 g, 88%). [00164] A mixture of 1 -benzyltetrahydrothiophenium bromide (3.39 g, 13.1 mmol) and (?)-methyl 3-(4-bromophenyl)acrylate (2.10 g, 8.71 mmol) in DCM (50 mL) was cooled to -78C and slowly treated with LiHMDS (13.1 mL, 1 M solution in THF) (via syringe pump, 1 mL/h). After complete addition, the mixture was warmed to r.t., stirred for 16 h and was quenched with H20 (50 mL). The biphasic mixture was separated and the organic layer washed with brine (2 x 50 mL), dried (MgS04) and concentrated. Purification by flash silica column chromatography (gradient elution i-hex to 5% EtOAc in i-hex) gave the title compound as a colourless oil (600 mg, 20%). LCMS (ES+) 332, 334 (M+H)+.

According to the analysis of related databases, 3650-78-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; LUCKHURST, Christopher, A.; BURLI, Roland, W.; STOTT, Andrew, J.; BRECCIA, Perta; WO2014/14900; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

820 mg (3.4 mmol) of methyl 4-bromocinnamate were dissolved in 7 ml of dry toluene, added with 116 mg (0.1 mmol) of Pd(PPh3J4, a solution of 374 mg (1.1 mmol) of 4- cyanobenzeneboronic acid in 2 ml of MeOH, 6.8 ml of 2M Na2CO3 in water, and refluxed 9 h. Addition of EtOAc, washing with water, then with brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures 9/1 gave 273 mg of methyl 3-(4-cyanobiphenylyl)acrylate, mp. 150-1520C.A solution of the above compound (270 mg, 1.02 mmol) and of 2-tetrahydropyranyl- O-hydroxylamine (117 mg, 1.02 mmol) in 14 ml THF was cooled at -780C, added with 1.07 ml of sodium hexamethyldisilazane, stirred 2 hrs, then heated at -2O0C, cooled again at – 780C, quenched with NH4CI, extracted with AcOEt, the extract evaporated and chromatographed (Merck silicagel) with Hexane/EtOAc 6/4 to give 189 mg of 2- EPO tetrahydropyranyloxyamide of 3-(4-cyanobiphenylyl)acrylic acid, as a white solid, mp. 211- 2130C.A solution of the above compound (187 mg, 0.54 mmol) in 5 ml of MeOH was treated with 30 mg (0.16 mmol) of p-toluenesulfonic acid, stirred 24 h at room temp, filtered and washed with MeOH, to give 96 mg of 3-(4-cyanobiphenylyl)acrylic acid hydroxyamide, mp. 212-2140C, Rf 0.3 (CH2CI2/MeOH 95/5), 1H NMR: (DMSO-d6): 6.54 (d, 1 H, -CH=, J = 15.3 Hz), 7.51 (d, 1 H, CH=, J = 15.3 Hz), 7.69 (d, 2H, 2Ar, J = 8.2 Hz), 7.82 (d, 2H, 2Ar, J = 8.2 Hz), 7.8-8.0 (m, 4H, 6Ar), 9.05 (s, 1 H, NH), 10.80 (s, 1 H, OH).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; WO2007/383; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics