Category: 136333-97-6

Related Products of 136333-97-6,Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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.

Example 11A Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl}ethyl]malonate At room temperature, 62.66 g (192 mmol) of cesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6] are added to a solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF. The mixture is then stirred at room temperature overnight. After the reaction has gone to completion, the reaction solution is evaporated to dryness, and the residue is taken up in water and extracted three times with ethyl acetate. The combined organic phases are then washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). This gives 41.35 g (83.6 mmol, 65% of theory) of a colorless solid. LC-MS (Method 2): Rt=2.92 min; m/z=495 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(2-bromoethyl)benzoate, its application will become more common.

Reference:
Patent; Hahn, Michael; Becker, Eva-Maria; Knorr, Andreas; Schneider, Dirk; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; Lang, Dieter; US2010/197680; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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 4-(2-bromoethyl)benzoate

8e) 4-(2-Bromoethyl)benzyl alcohol To a suspension of LiAIH4 (4.5 mmol; 0.172 g) in anhydrous THF(5.0 ml) cooled to 00C was added dropwise a solution of methyl 4-(2- bromoethyl)benzenecarboxylate (1.0 g; 4.1 mmol) in anhydrous THF(10.0 ml). The reaction mixture was stirred for 5 minutes at room temperature and, after adding ice, was filtered through a Bchner filter.The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (3 * 100 ml). The combined organic phases were washed with saturated NaCI solution, dried over sodium sulfate and evaporated under reduced pressure. 800 mg (82.6%) of pure product were thus obtained as an oil .1H NMR (CDCI3, delta ppm): 3.22 (t, 2H); 3.62 (t, 2H); 4.72 (s, 2H); 7.25- 7.39 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 136333-97-6, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A.; ALISI, Maria Alessandra; CAZZOLLA, Nicola; COSTI, Roberta; DI SANTO, Roberto; FURLOTTI, Guido; GUGLIELMOTTI, Angelo; POLENZANI, Lorenzo; WO2010/12611; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 136333-97-6,Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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.

Example 11A Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl}ethyl]malonate At room temperature, 62.66 g (192 mmol) of cesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6] are added to a solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF. The mixture is then stirred at room temperature overnight. After the reaction has gone to completion, the reaction solution is evaporated to dryness, and the residue is taken up in water and extracted three times with ethyl acetate. The combined organic phases are then washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). This gives 41.35 g (83.6 mmol, 65% of theory) of a colorless solid. LC-MS (Method 2): Rt=2.92 min; m/z=495 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(2-bromoethyl)benzoate, its application will become more common.

Reference:
Patent; Hahn, Michael; Becker, Eva-Maria; Knorr, Andreas; Schneider, Dirk; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; Lang, Dieter; US2010/197680; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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. category: esters-buliding-blocks

8e) 4-(2-Bromoethyl)benzyl alcohol To a suspension of LiAIH4 (4.5 mmol; 0.172 g) in anhydrous THF(5.0 ml) cooled to 00C was added dropwise a solution of methyl 4-(2- bromoethyl)benzenecarboxylate (1.0 g; 4.1 mmol) in anhydrous THF(10.0 ml). The reaction mixture was stirred for 5 minutes at room temperature and, after adding ice, was filtered through a Bchner filter.The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (3 * 100 ml). The combined organic phases were washed with saturated NaCI solution, dried over sodium sulfate and evaporated under reduced pressure. 800 mg (82.6%) of pure product were thus obtained as an oil .1H NMR (CDCI3, delta ppm): 3.22 (t, 2H); 3.62 (t, 2H); 4.72 (s, 2H); 7.25- 7.39 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 136333-97-6, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A.; ALISI, Maria Alessandra; CAZZOLLA, Nicola; COSTI, Roberta; DI SANTO, Roberto; FURLOTTI, Guido; GUGLIELMOTTI, Angelo; POLENZANI, Lorenzo; WO2010/12611; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, 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. Computed Properties of C10H11BrO2

EXAMPLE 13({[(1Z)-2,2-Diethyl-1-oxidohydrazono]amino}oxy)methyl 4-{2-[({2-chloro-5-[(2-methyl-2,3-dihydro-1H-indol-1-yl)carbamoyl]phenyl}sulphonyl)amino]ethyl}benzoateStep A: Methyl 4-{2-[(tert-butoxycarbonyl)({2-chloro-5-[(2-methyl-2,3-dihydro-1H-indol-1-yl)carbamoyl]phenyl}sulphonyl)amino]ethyl}-benzoateDissolve the compound obtained in Step A of Example 1 (1.04×10-2 mol) in acetonitrile (20 ml) and place the solution under stirring. Add diisopropylethylamine (1.24×10-2 mol) and then, after stirring for 10 minutes, intermediate 9 (2.20×10-2 mol) dissolved in acetonitrile (20 ml). Heat the mixture at 60 C. After 5 days, the reaction mixture is evaporated to dryness under reduced pressure. The residue obtained is chromatographed on a silica column using as eluant a 75/25 n-heptane/ethyl acetate mixture.The title product is obtained in the form of a pale yellow meringue.

The synthetic route of Methyl 4-(2-bromoethyl)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; US2010/286225; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 136333-97-6, The chemical industry reduces the impact on the environment during synthesis 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, I believe this compound will play a more active role in future production and life.

[8911 Step 1: Synthesis of methyl4-(2-((3R.55?)-4-benzvl-3 .5-dimethvlpiperazin- 1 -vflethvl?)benzoate [8921 (2S,6R)-1-benzyl-2,6-dimethylpiperazine (formula 8-3, 0.200 g, 0.83 1 mmol) and DIPEA (0.363 mL, 2.077 mmol) were dissolved in acetonitrile (5 mL), and methyl 4-(2-bromoethyl)benzoate (formula 8-4, 0.404 g, 1.66 1 mmol) was added thereto at room temperature. The mixture was stirred at 60 C for 17 hours, and then water was added to the reaction mixture, followed by extraction with methylene chloride. The extract was passed through a plastic filter to remove solid residue and an aqueous layer, and the organic layer was concentrated under reduced pressure. The concentrate was concentrated by column chromatography (silicon dioxide; ethyl acetate/hexane = 25 %) and concentrated to afford the desired compound (0.075 g, 24.6 %) as a pale yellow oil.

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-(2-bromoethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; SONG, Hyeseung; LEE, Changgon; KWAK, Dalyong; LEE, Jaeyoung; BAE, Suyeal; KIM, Yuntae; BAE, Daekwon; HA, Nina; BAE, Miseon; KIM, Jihyun; WO2015/137750; (2015); 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. 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 4-(2-bromoethyl)benzoate

Example 4A Diallyl 2-[4-(methoxycarbonyl)phenyl]ethylmalonate Under argon and at 0 C., 4.44 g (111.0 mmol) of sodium hydride (60% strength dispersion in mineral oil) are added a little at a time to a solution of 27.28 g (148.09 mmol) of diallyl malonate in 220 ml of anhydrous dioxane. The mixture is stirred at 40 C. for 30 min, and a solution of 18.00 g (74.04 mmol) of methyl 4-(2-bromoethyl)benzoate is then added at room temperature. The reaction mixture is then heated at 110 C. for 16 hours. After addition of 25 ml of saturated ammonium chloride solution, most of the dioxane is removed on a rotary evaporator. The residue is taken up in 200 ml of ethyl acetate and 100 ml of water. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After distillative removal of a large proportion of the excess diallyl malonate, the crude product is pre-purified on 100 g of silica gel 60 (mobile phase: cyclohexane/dichloromethane 2:1, then cyclohexane/ethyl acetate 4:1). The desired product is then isolated by preparative HPLC. This gives 11.60 g (22% of theory) of a colorless oil. LC-MS (method 2): Rt=2.53 min; MS (ESIpos): m/z=347 [M+H]+. 1H-NMR (400 MHz, CDCl3): delta=2.26 (m, 2H), 2.73 (t, 2H), 3.40 (t, 1H), 3.91 (s, 3H), 4.63 (d, 4H), 5.25 (d, 2H), 5.33 (d, 2H), 5.90 (m, 2H), 7.25 (d, 2H), 7.96 (d, 2H).

According to the analysis of related databases, 136333-97-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER HEALTHCARE AG; US2009/286882; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 136333-97-6, A common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, 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.

[0487] Scheme 3 , Step I: Preparation of (i?)-methyl 4-(2-(5 -(((tert- butyldimethylsilyl)oxy)methyl)-3 ,3 -difluoro-2-oxopyrrolidin- 1 -yl)ethyl)benzoate (lib; PG=TBS) [0488] To a suspension consisting of sodium hydride (60% in mineral oil, 61 mg, 1.5 mmol) and sodium iodide (251 mg, 1.67 mmol) in DMF (40 mL) was added dropwise a solution consisting of (i?)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoropyrrolidin-2- one (intermediate 9; PG=TBS, 370 mg, 1.39 mmol) in DMF (5 mL). The mixture was stirred at room temperature for two hours followed by 50C for 30 minutes. To the reaction mixture was added dropwise methyl 4-(2-bromoethyl)benzoate (406 mg, 1.67 mmol) in DMF (5 mL), and stirring continued overnight at 50C. The mixture was diluted with ethyl acetate and washed sequentially with 0.5 N hydrochloric acid, a 5% aqueous solution of sodium thiosulfate, 50% brine, and brine. The organic phase was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography. Elution with ethyl acetate :heptane (increasing solvent strength, 1 :50 v/v to 1 : 10 v/v) followed by eluting with methanol-dichloromethane (1 :50 v/v) afforded the title intermediate (39 mg, 6.6%); TLC R/ 0.6 (solvent system: 70:30 v/v heptane:ethyl acetate); -NMR (CDC13) delta 7.9 (d, 2H), 7.28 (d, 2H), 3.98-3.91 (m, 1H), 3.9 (s, 3H), 3.74-3.48 (m, 2H), 3.46-3.35 (m, 2H), 3.1-2.9 (m, 2H), 2.48-2.18 (m, 2H), 0.8 (s, 9H), 0.0 (s, 6H); MS (ESf ) m/z 445.1 (M+NH3). [0489] Significant improvement of the yield (in relation to (R)-5-(((tert- butyldimethylsilyl)oxy)methyl)-3,3-difluoropyrrolidin-2-one) was realized by repeated additions of sodium hydride and methyl 4-(2-bromoethyl)benzoate to the reaction mixture.

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; CAYMAN CHEMICAL COMPANY, INC.; MYOMETRICS, LLC; BARRETT, Stephen, Douglas; CISKE, Fred, Lawrence; COLOMBO, Joseph, Michael; ENDRES, Gregory, William; GERMAIN, Bradlee, David; KORNILOV, Andriy; KRAMER, James, Bernard; UZIEBLO, Adam; OWEN, Thomas, Allen; O’MALLEY, James, Paul; WO2014/15246; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics