4224-69-5 Archives - Esters-buliding-blocks

September 27, 2021 News Some tips on 4224-69-5

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-(bromomethyl)acrylate, other downstream synthetic routes, hurry up and to see.

Electric Literature of 4224-69-5, 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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To an anhydrous THF solution (2 ml) of the above-obtained Compound (8) (A=-CH=CH-CH=CH-, PG=TBS, 24(E)) (48 mg, 76.8 mumol) were added zinc (powder) (8 mg, 0.12 mmol), methyl 2-(bromomethyl)acrylate (13.8 mul, 0.12 mmol) and a saturated ammonium chloride aqueous solution (0.7 ml) at 0C, and the mixture was stirred for 30 min at room temperature. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by column chromatography (5%?20% ethyl acetate in hexane) to obtain Compound (C) (60 mg, 107% yield). Compound (C):1H NMR (CDCl3) delta : 0.055 (s, 3 H), 0.059 (s, 3 H), 0.062 (s, 6 H), 0.55 (s, 3 H), 0.88 (s, 18 H), 1.04 (d, J=6.6 Hz, 3 H), 1.23-2.17 (m, 15 H), 2.18-2.24 (m, 1 H), 2.42-2.52 (m, 2 H), 2.60-2.65 (m, 1 H), 2.78-2.86 (m, 1 H), 3.74 (s, 3 H), 4.19-4.22 (m, 1 H), 4.28-4.34 (m, 1 H), 4.34-4.39 (m, 1 H), 4.86 (d, J=2.2 Hz, 1 H), 5.17 (s, 1 H), 5.53-5.62 (m, 1 H), 5.67 (d, J=1.2 Hz, 1 H), 5.90-6.03 (m, 2 H), 6.15-6.25 (m, 2 H), 6.26 (d, J=1.2 Hz, 1 H). MS m/z 747 (M+23)+.

Reference:
Patent; TEIJIN LIMITED; EP1477483; (2004); A1;,
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15-Sep-2021 News Introduction of a new synthetic route about 4224-69-5

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 2-(bromomethyl)acrylate

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sources of common compounds: 4224-69-5

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.

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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, A new synthetic method of this compound is introduced below., Computed Properties of C5H7BrO2

General procedure: To a 20 mL two-necked round-bottom flask attached with areflux condenser were added V-65 (25 mg, 0.1 mmol) and K2CO3(138 mg, 1.0 mmol), and this flask was purged with argon.Then, 1-nonanal (1a, 71 mg, 0.5 mmol), methyl 2-(bromomethyl)acrylate (2a, 269 mg, 1.5 mmol), and degassedbenzene (5 mL) were added. The mixture was stirred at 60 C for1 h. The reaction mixture was filtered through a short plug ofCelite, and the filtrate was concentrated under reduced pressure.The residue was purified by flash column chromatographyon SiO2 (hexane/EtOAc = 1:0 to 30:1) and preparative HPLC(chloroform) to give methyl 2-methylene-4-oxododecanoate(3b, 101 mg, 84%).

Reference:
Article; Kippo, Takashi; Kimura, Yuki; Ueda, Mitsuhiro; Fukuyama, Takahide; Ryu, Ilhyong; Synlett; vol. 28; 14; (2017); p. 1733 – 1737;,
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Share a compound : 4224-69-5

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Electric Literature of 4224-69-5, 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 4224-69-5 as follows.

To a dry nitrogen-flushed 15 mL round bottom flask was added dry THF (5.9 mL) and iPr2NH(0.87 mL, 6.21 mmol, 1.05eq.). The flask was cooled to -78 C andn-BuLi(2.48 mL, 6.21 mmol, 1.05eq.) was added slowly. The mixture wasstirred at 0 C for 10 minutes and then cooled back down to -78 C and cannulated into a -78 C solution of starting material(1.16 g, 5.91 mmol, 1.00eq.) in THF (5.9 mL).The reaction mixture was stirred for 30 min at -78 C and then methyl(2-bromomethyl)acrylate wasadded (0.87 mL, 7.09 mmol,1.20 eq.) via syringe. The reaction wasstirred for 1h at -78 C then 3 h at r.t. The reaction was quenched with H2O(10 mL) and extracted with Et2O (2 x 20 mL). The combinedorganics were washed with brine (10 mL), dried withMgSO4, rotovapped, and chromatographedto yield the desired product was a white solid (1.5338 g, 5.21 mmol) in 88% yield. 1H NMR (300 MHz, CDCl3)delta 8.03 – 7.91 (m, 2H), 7.47-7.38 (m, 1H), 7.36 – 7.13 (m, 7H), 6.07 (s,1H), 5.41 (s, 1H), 4.95 (t, J = 7.2Hz, 1H), 3.71 (s, 3H), 3.23 (dd, J = 14.1, 7.3 Hz, 1H), 2.79 (dd, J = 14.0, 7.2 Hz, 1H).. 13C NMR (75 MHz, CDCl3) delta 198.7, 167.2, 138.7,137.3, 136.5, 132.8, 128.8, 128.6, 128.4, 128.2, 128.0, 127.9, 127.1, 52.2,51.8, 36.7.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ramachandran, P. Veeraraghavan; Helppi, Matthew A.; Lehmkuhler, Arlie L.; Marchi, Jennifer M.; Schmidt, C. Max; Yip-Schneider, Michele T.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 19; (2015); p. 4270 – 4273;,
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Ester – an overview | ScienceDirect Topics

Discovery of 4224-69-5

Synthetic Route of 4224-69-5, The chemical industry reduces the impact on the environment during synthesis 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, I believe this compound will play a more active role in future production and life.

(7E)-(1R,3R,20R)-1,3-di-(tert-butyldimethylsilyloxy)-2-methylene-9,10-seco-19-nor-20-[(2S)-hydroxy-4-methoxycarbonyl-4-penten-1-yl]-5,7-pregnandiene (10) and (7E)-(1R,3R,20R)-1,3-di-(tert-butyidimethylsilyloxy)-2-methylene-9,10-seco-19-nor-20-[(2R)-hydroxy 4-methoxycarbonyl-4-penten-1-yl]-5,7-pregnandiene (1); To a solution of 9 (25 mg, 425 mumol) in saturated aqueous NH4Cl solution/THF (5:1, 3 mL) were added methylbromomethylacrylate (10 muL, 85 mumol) (commercially available from Sigma-Aldrich) and activated Zn dust (11 mg, 0.17 mmol) at 0 C., and the mixture was stirred at the same temperature for 1.5 hours. The mixture was diluted with EtOAc. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated. The residue was purified by flash column chromatography on silica gel (5% EtOAc/hexanes) to give 10 (5 mg, 7.3 mumol, 57%) and 11 (4 mg, 5.5 mumol, 43%) as colorless oils, respectively. 10: 1H NMR (CDCl3, 400 MHz) delta 6.25(s, 1H, =CH2), 6.21 (d, J=11.2 Hz, 1H, 6-H), 5.84 (d, J=11.2 Hz, 1H, 7-H), 5.67 (s, 1H, =CH2), 4.97 (s, 1H, =CH2), 4.91 (s, 1H, =CH2), 4.42 (m, 2H, 1beta- and 3alpha-H), 3.87 (m, 1H, CH-OH), 3.77 (s, 3H, -CO2CH3), 2.82 (br d, J=11.3, 1H), 2.56-2.44 (m, 3H), 2.40-2.25 (m, 2H), 2.18 (m, 1H), 0.97 (d, J=6.6 Hz, 3H), 0.90 (s, 9H, Si-t-Bu), 0.85 (s, 9H, Si-t-Bu), 0.57 (s, 3H), 0.08, 0.06, 0.05, and 0.02 (each s, each 3H, 4× SiCH3); 13C NMR (CDCl3) delta 168.31, 153.19, 141.28, 137.76, 133.03, 127.92, 122.58, 116.41, 106.44, 72.79, 71.78, 67.85, 57.35, 56.54, 52.28, 47.85, 46.00, 43.93, 41.78, 40.86, 38.72, 33.09, 28.94, 28.08, 26.04, 25.97, 23.62, 22.44, 18.87, 18.45, 18.35, 12.35, -4.67 (SiMe), 4.90 (3× SiMe); exact mass calculated for C40H70O5Si2Na [M+Na]+ 709.4660, found 709.4680. 11: 1H NMR (CDCl3, 400 MHz) delta 6.29 (s, 1H, =CH2), 6.22 (d, J=11.1 Hz, 1H, 6-H), 5.84 (d, J=11.1 Hz, 1H, 7-H), 5.70 (s, 1H, =CH2), 4.98 (s, 1H, =CH2), 4.93 (s, 1H, =CH2), 4.43 (m, 2H, 1beta- and 3alpha-H), 3.90 (m, 1H, CH-OH), 3.79 (s, 3H, -CO2CH3), 2.84 (br d, J=12.1 Hz, 1H), 2.71 (dd, J=13.8, 1.7 Hz, 1H), 2.56-2.42 (m, 2H), 2.34 (m, 1H), 1.03 (d, J=6.4 Hz, 3H), 0.90 (s, 9H, Si-t-Bu), 0.87 (s, 9H, Si-t-Bu), 0.57 (s, 3H), 0.09, 0.08, 0.06, and 0.04 (each s, each 3H, 4× SiCH3); 13C NMR (CDCl3), delta 168.30, 153.17, 141.23, 137.77, 133.04, 128.07, 122.58, 116.41, 106.46, 72.72, 71.83, 69.45, 57.47, 56.43, 52.28, 47.80, 45.91, 44.13, 40.81, 40.27, 38.77, 34.39, 28.93, 28.12, 26.03, 25.98, 23.61, 22.42, 19.55, 18.74, 18.37, 12.29, -4.67 (3× SiMe), -4.88 (SiMe); exact mass calculated for C40H70O5Si2 [M]+ 686.4762, found 686.4789.

Reference:
Patent; Wisconsin Alumni Research Foundation; US2006/223782; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Discovery of 4224-69-5

Reference:
Patent; Wisconsin Alumni Research Foundation; US2006/223782; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Simple exploration of Methyl 2-(bromomethyl)acrylate

Adding a certain compound to certain chemical reactions, such as: 4224-69-5, name is Methyl 2-(bromomethyl)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 4224-69-5, Computed Properties of C5H7BrO2

A 250 mL three-necked flask was evacuated with nitrogen to protect it, and the milled magnesium bars (2.06 g, 84.64 mmol) and THF (40 mL) were added in this order.Turn on stirring, heat to 45 ~ 55 C and add a piece of iodine under reflux to turn into a red-brown solution.The compound of formula 1 (9.2 g, 42.32 mmol) was dissolved in 26 mL of tetrahydrofuran,Then slowly add 20 drops to the reaction system,When the reaction system solution has a reddish brown color, it turns into a yellow emulsion until it turns into a white solution.As the reaction proceeds, the reaction system solution will become a clear and transparent liquid.After the addition, the reaction was performed for 0.5 h to obtain a compound of formula 2.; A 500 mL round-bottomed flask was evacuated with nitrogen, and the compound of formula 3 (5.00 g, 27.93 mmol),THF (80 mL), CuI (8.38 mmol, 1.60g) and LiCl (55.86 mmol, 2.37g),The reaction system was placed in an ice-water bath at 0 C.The compound of formula 2 obtained by the reaction was added dropwise to the reaction system. After the addition, the reaction was carried out for 0.5 h, and the reaction was moved to room temperature for 2 h.After the reaction was completed, an appropriate amount of water was added, followed by extraction with ethyl acetate (40 mL × 3) three times. The organic phases were combined, washed with saturated brine, and dried over anhydrous sodium sulfate.Suction filtration, the filtrate was concentrated under reduced pressure, the crude product was separated and purified by silica gel column (eluent: petroleum ether: ethyl acetate = 30: 1)The compound of formula 4 (5.39 g, yield 82%) was obtained as a colorless oily liquid.

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; Shanxi Tumor Institute; Yang Xihua; Ou Wentao; (17 pag.)CN110776488; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Continuously updated synthesis method about 4224-69-5

Electric Literature of 4224-69-5, These common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, 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.

The solution of aldehyde 8 (13.0 g, 25 mmol) in THF (80mL) was mixed with saturated solution of NH4Cl (100 mL)and Zn dust (1.6 g, 50 mmol) at the room temperature. Themixture was stirred and the methyl 2-(bromomethyl)acrylate (7.2 g, 40 mmol) was added inseveral portions. The mixture was stirred for 1 hour, diluted with diethyl ether (900 mL), washedby brine (2×150 mL) and dried over Na2SO4. The solvents were evaporated and the product waspurified by column chromatography (EtOAc:hexane 1:2) to obtain 9 (13.4 g, 87%) as a colorlessliquid, diastereomeric mixture (~0.43:0.54 labeled as A and B).

Statistics shows that Methyl 2-(bromomethyl)acrylate is playing an increasingly important role. we look forward to future research findings about 4224-69-5.

Reference:
Article; Baranov, Mikhail S.; Kaskova, Zinaida M.; Grit?enko, Roman; Postikova, Svetlana G.; Ivashkin, Pavel E.; Kislukhin, Alexander A.; Moskvin, Dmitrii I.; Mineev, Konstantin S.; Arseniev, Alexander S.; Labas, Yulii A.; Yampolsky, Ilia V.; Synlett; vol. 28; 5; (2017); p. 583 – 588;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Simple exploration of C5H7BrO2

Application of 4224-69-5, A common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, molecular formula is C5H7BrO2, 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: Methylcis-4-hydroxy-2-methylene-3,4-diphenylbutanoate2: Starting material (8.583 g, 33.64mmol, 1.0 eq.) was weighed out in a 250 mL round bottom flask. To it was addedTHF (50 mL, 0.66 M), H2O (33.6 mL, 1.0 M), and benzaldehyde (5.14mL, 50.47 mmol, 1.5 eq.). Finally indiumpowder (5.02 g, 43.74 mmol, 1.3 eq.) was added and the reaction mixture wascapped to prevent solvent evaporation and stirred overnight (17 h). TLCanalysis was used to verify completion of the reaction. Upon completion, the reaction mixture wastransferred into a separatory funnel with Et2O (100 mL) and H2O(100 mL). If an emulsion formed, 1M HClwas added until the emulsion broke up. Afterseparation of the layers, the aqueous layer was extracted with Et2O(2 x 100 mL). The combined organic layers were washed with brine (100 mL) anddried over MgSO4. Evaporationof solvent en vacuo followed bycolumn chromatography over silica gel (SiO2) yielded the desired productas a viscous clear oil (8.575 g, 30.37 mmol, 90.3 %).

The synthetic route of 4224-69-5 has been constantly updated, and we look forward to future research findings.

Share a compound : Methyl 2-(bromomethyl)acrylate

Related Products of 4224-69-5, 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 4224-69-5 as follows.

Cyclopentylamine (5.79 mL, 58.7 mmol, 3.00 eq) and triethylamine (2.73 mL, 19.6 mL, 1.00 eq) were added to DCM (98 mL) and the reaction was cooled to 0 C. Methyl 2-(bromomethyl)acrylate (2.35 mL, 19.6 mmol, 1.00 eq) in DCM (48 mL) was added dropwise. Following addition the reaction was stirred for an additional 30 minutes at 0 C. Water was added and the layers separated. The aqueous layer was extracted with an additional portion of DCM and the combined organics were dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using 0- 60% DCM/MeOH/NH4OH (89: 10: 1) afforded 1.19 g (33%) of the title compound as a clear oil: 1H MR (400 MHz, DMSO-d6) 3 6.10 (s, 1H), 5.79 (s, 1H), 3.67 (s, 3H), 3.65 (d, J= 5.9 Hz, 1H), 3.56 (d, J= 15.1 Hz, 1H), 3.21 (d, J= 7.4 Hz, 1H), 2.98 (p, J= 6.2 Hz, 1H), 1.72-1.22 (m, 8H); ES-MS [M+l]+: 184.4.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; NISWENDER, Kevin; (90 pag.)WO2017/117556; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics