Category: 148547-19-7

Synthetic Route of 148547-19-7, 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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of methyl 4-bromo-3-methylbenzoate (ABCR, 5 g, 21.8 mmol) in dry 1 ,4- dioxane(100 ml_), were added dry Cs2CO3 (10.65 g, 32.7 mmol) and piperidine (2.2 g, 26 mmol). The mixture was degassed with N2 for 10 min. BINAP (0.67 g, 1.1 mmol) and palladium(ll)acetate (0.24 g, 1.1 mmol) were added under N2 and the resulting mixutre was refluxed for 15h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The crude product was purified by flash chromatography, affording the title product as a off-white solid (4.9 g, 96%). 1H NMR (CDCI3, 400 MHz) delta 7.82-7.84 (m, 2H), 6.97-6.99 (d, 1 H), 3.92 (s, 3H), 2.90-2.93 (m, 4H), 1.67-1.76 (m, 4H), 1.62-1 .63 (m, 2H). LC/MS (Method A): 233.9 (M+H)+. HPLC (Method B) Rt 4.18 min (Purity: 95.4%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-3-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 148547-19-7, 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 148547-19-7 as follows.

To a solution of methyl 4-bromo-3-methylbenzoate (ABCR, 15 g, 65 mmol) in toluene (200 ml.) and water (200 ml_), was added o-tolylboronic acid (10.68 g, 78 mmol) followed by potassium carbonate (45.25 g, 32.7 mmol) and Pd(PPh3)4 (3.78 g, 3.3 mmol). The mixture was degassed with N2 and refluxed at 1200C for 6 hours. After the completion of reaction, the reaction mixture was cooled to RT. The organic phase was separated and evaporated under reduced pressure. The crude compound was passed through a silica column (60-120) using hexane as eluent to get the title compound as a white solid (15 g, 95%). 1H NMR (DMSO-dbeta, 400 MHz) delta 7.91 (s, 1 H), 7.83-7.81 (m, 1 H), 7.33-7.30 (m, 2H), 7.28-7.26 (m, 1 H), 7.25-7.22 (m, 1 H), 7.07-7.05 (d, 1 H), 3.86-3.81 (s, 3H), 2.09-2 (s, 3H), 1.97-1.92 (s, 3H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; GERBER, Patrick; DORBAIS, Jerome; WO2010/100142; (2010); A1;,
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 148547-19-7 as follows. category: esters-buliding-blocks

The compound 120a (1.0 g, 4.365 mmol) was dissolved in 1,4-dioxane (30 mL), and the compound 120b (2.22 g, 8.73 mmol), KOAc (1.5 g, 15.277 mmol), and PdCl2 were added. (dppf) (0.32 g, 0.436 mmol) and,Nitrogen was replaced three times, and then the reaction solution was stirred at 95 C for 16 hours. Cool to room temperature, add water (60 mL),Extracted with ethyl acetate (30 mL x 3), combined the organic layers and washed with water (30 mL x 2), dried over MgSO4, filtered and concentrated,The concentrate was purified by silica gel chromatography (ethyl acetate: petroleum ether = 0-10%) to obtain a white off-white compound 120c, 3-methyl-4- (4,4,5,5-tetramethyl-1, Methyl 3,2-dioxaborolan-2-yl) benzoate (1.113 g, yield 92.4%).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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 148547-19-7, Formula: C9H9BrO2

A suspension of methyl 4-bromo-3-methylbenzoate (ABCR AV19078; 3 g; 13.10 mmol; 1 eq.), 2-(trifluoromethyl)phenylboronic acid (Aldrich 393606; 2.74 g; 14.41 mmol; 1.10 eq.), potassium carbonate (9.05 g; 65.48 mmol; 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol; 0.10 eq.) in toluene (15 ml_) and water (15 ml_) was refluxed for 3 hours. The resulting mixture was filtered through a short pad of Celite, which was further washed with toluene. After evaporation of the solvent, the residue was taken up in ethyl acetate and washed successively with sat. aq. NaHCC>3, water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (3.7 g, 96%) as a brown oil. HPLC (Method A) : Rt 5.34 min (purity 70.9%). LC/MS : 294.9 (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; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 148547-19-7,Some common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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.

A mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24. 88-MMOL), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3 * 100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product is taken up in propionitrile (100 mL). Methyl acrylate (10 mL, 121.5 mmol), palladium acetate (1.12 g, 5 mmol), tri-o-tolylphosphine (3.0 g, 10 mmol), and N, N-diisopropyl ethylamine (8.7 mL, 50 mmol) are sequentially added and the resulting reaction mixture is heated to 110 C 3 hr. The mixture is concentrated, and the residue diluted with aqueous hydrochloric acid (100 ML, 1M). The product is extracted with dichloromethane (2 * 100 mL) and ethyl acetate (100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 7: 3 hexanes: ethyl acetate to 1 : 1 hexanes: ethyl acetate to afford the pure product as a yellow oil, 4.7 g, 91 %. MS M+1 207. The structure is confirmed by : L H NMR spectroscopy.

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/63184; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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.

To a stirred solution of methyl 4-bromo-3-methylbenzoate (5g, 21.8 mmol) in dry 1 ,4- dioxane(100 ml_), were added dry Cs2CO3 (10.65 g, 32.7 mmol) and morpholine (2.3 g, 26 mmol). The mixture was degassed for 10 min. BINAP (0.67 g, 1.1 mmol) and palladium(ll)acetate (0.24 g, 1.1 mmol) were added under N2 and the resulting mixutre was refluxed for 15h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The crude product was purified by flash chromatography, affording the title compound as a yellow solid (4.3 g, 84%). 1H NMR (CDCI3, 400 MHz) delta 7.86-7.90 (m, 2H), 7.13-7.16 (d, 1 H), 3.98-4.0 (m, 4H), 3.91 (3H, s), 3.10-312 (m, 4H), 2.45 (3H, s). LC/MS (Method A): 236.0 (M+H)+. HPLC (Method B) Rt 2.24 min (Purity: 95.3%).

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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.

A mixture of methyl 4-bromo-3-methylbenzoate (20.0 g, 87.3 mmol), 2- (trifluoromethyl)benzeneboronic acid (24.9 g, 131.0 mmol), potassium carbonate (24.1 g, 174.6 mmol) and bis(tricyclohexylphosphine)palladium (II) dichloride (64.5 mg, 0.09 mmol) was prepared in dioxane (200 ml.) and water (50 ml.) under N2 atmosphere. The mixture was heated at 1000C for 3 hours. A 5N aqueous solution of NaOH (100 ml.) was added and the reaction mixture was stirred at 1000C for one additional hour. The reaction mixture was cooled at RT and the aqueous layer was removed. The organic layer was filtered through a Celite pad, concentrated until 75 ml under reduced pressure, diluted with water (125 ml) and washed with MTBE (2×200 ml_). The aqueous layer was acidified with a 5N aqueous solution of HCI (25 ml, pH~1 ) and extracted with MTBE (2×100 ml). The organic layers were combined, dried (Na2SO4) and filtered through a Celite pad. The solution was concentrated until 100 ml_, then heptane was added (200 ml_). The mixture was concentrated until 100 ml_. The precipitate was filtered off and rinsed twice with heptane, then dried under reduced pressure to give the title compound as a white powder (22.5 g, 92%). HPLC (Method A), Rt: 4.4 min (purity: 100%). UPLC/MS, M-(ESI): 279.0. 1H NMR (DMSO-d6, 300 MHz) delta 13.00 (s, 1 H), 7.87 (m, 2H), 7.80 (dd, J=7.9, 1.6 Hz, 1 H), 7.75 (m, 1 H), 7.64 (m, 1 H), 7.34 (d, J=7.6 Hz, 1 H), 7.23 (d, J=7.9 Hz, 1 H), 2.02 (s, 3H).

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; MERCK SERONO S.A.; QUATTROPANI, Anna; GERBER, Patrick; DORBAIS, Jerome; WO2010/100142; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 148547-19-7, 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 148547-19-7 as follows.

BINAP (0.67 g; 1.1 mmol; 0.05 eq.) and palladium acetate (0.24 g; 1.1 mmol; 0.05 eq.) were added to a suspension methyl 4-bromo-3-methylbenzoate (5 g; 21.8 mmol; 1 eq.), CS2CO3 (10.65 g; 32.7 mmol; 1 .5 eq.) and piperidine (2.2 g; 26 mmol; 1.2 eq.) in dioxane (100 mL) and the reaction mixture was refluxed for 15 hours. After filtration through a pad of Celite, the solution was concentrated in vacuo and the residue purified by column chromatography (petroleum ether/ethyl acetate, 80/20) to afford the title compound (4.9 g, 96%) as a brown solid.LC/MS : 233.9 (M+H)+. 1H NMR (CDCI3, 400 MHz) delta 7.84-7.82 (m, 2H), 6.99-6.97 (m, 1 H), 3.92 (s, 3H), 2.93-2.90 (m, 4H),1.76-1.67 (m, 4H, m), 1.63-1.62 (m, 2H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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.

4-Bromo-3-methylbenzylalcohol (4) A solution of methyl 4-bromo-3-methylbenzoate (2.0 g, 8.7 mmol) in dry THF (10 mL) was added to an ice-cooled suspension of lithium aluminiumhydride (400 mg, 10.4 mmol) in dry THF (30 mL). After addition, the mixture was warmed to room temperature and then stirred for 3 h. The excess lithium aluminiumhydride was quenched by successive addition of water (0.4 mL), 15% NaOHaq (0.4 mL), and water (1.2 mL) under ice cooling. The insoluble material appeared was removed by filtration (celite), and the precipitate was washed by AcOEt (20 mL*5). The combined filtrates were washed with brine (50 mL) and then dried over Na2SO4. The solvent was evaporated, and the obtained product (1.6 g, 100%) was used for next step without further purification. 1H-NMR (CDCl3, 400 MHz): delta7.53 (1H, d, J=8.1 Hz), 7.26 (1H, d, J=1.5 Hz), 6.40 (1H, dd, J=8.1, 1.5 Hz), 4.68 (2H, s), 2.44 (3H, s).

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHANG, Christopher J.; VAN DE BITTNER, Genevieve V.; HIRAYAMA, Tasuku; CHAN, Jefferson; US2014/51863; (2014); 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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 148547-19-7

2l2′-dimethyl-1 l1 ‘-biphenyl-4-carboxylic acidStep 1: methyl 2,2′-dimethyl-1, 1’-biphenyl-4-carboxylate To a solution of methyl 4-bromo-3-methylbenzoate (ABCR, 15 g, 65 mmol) in toluene (200 mL) and water (200 mL), was added o-tolylboronic acid (10.68 g, 78 mmol) followed by potassium carbonate (45.25 g, 32.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.78 g, 3.3 mmol). The mixture was degassed with N2 and refluxed at 120 C for 6 hours. After the completion of reaction, the reaction mixture was cooled to RT. The organic phase was separated and evaporated under reduced pressure. The crude compound was passed through a silica column using hexane as eluent to get the title compound as a white solid (15 g, 95%). 1H NMR (DMSO-d6, 400 MHz) delta 7.91 (s, 1 H), 7.83-7.81 (m, 1 H), 7.33-7.30 (m, 2H), 7.28-7.26 (m, 1 H), 7.25-7.22 (m, 1 H), 7.07-7.05 (m, 1 H), 3.86-3.81 (s, 3H), 2.09-2 (s, 3H), 1.97-1.92 (s, 3H). HPLC (Method B), Rt: 3.01 min (purity: 98.71 %).

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 148547-19-7.

Reference:
Patent; MERCK SERONO S.A.; MUZERELLE, Mathilde; QUATTROPANI, Anna; MONTAGNE, Cyril; DORBAIS, Jerome; WO2010/69949; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics