Extended knowledge of Methyl 4-bromo-3-fluorobenzoate

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Related Products of 849758-12-9,Some common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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 4-bromo-3-fluoro-benzoic acid methyl ester (10 g, 43 mmol), bis(pinacolato)diboron (13.7 g, 54 mmol) and potassium acetate (12.7 g, 129 mmol) in dimethylsulfoxide (100 ml) was purged with argon, followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.5 g, 4.3 mmol). The mixture was heated at 80 C. for 3 h. After this time the mixture was cooled to 25 C., washed with water, extracted with ethyl acetate and concentrated. The resulting black oil was redissolved in ethyl acetate:hexanes 1:2 and filtered through a short pad of silica gel (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company). The filterate was concentrated in vacuo to afford 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (12 g, 99%) as a solid which was used in the next step without further purification.

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berthel, Steven Joseph; Chen, Li; Corbett, Wendy Lea; Feng, LiChun; Haynes, Nancy-Ellen; Kester, Robert Francis; So, Sung-Sau; Tilley, Jefferson Wright; US2011/144105; (2011); A1;,
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The origin of a common compound about 849758-12-9

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 849758-12-9, A common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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 4-Bromo-3-fluorobenzoic acid methyl ester (700mg; 2. 45MMOL) was dissolved in acetonitrile (3. 0ML) and placed into a 2ml microwave vessel. To the solution was added 1.5 eq OF BIS (PINACOLATO) diboron (3. 67mmol ; 1. 08G). The mixture was stirred on a magnetic stir plate until dissolution. To the mixture was added KOAC (7. 33mmol ; 7. 16MG) and 60MG of [1,1′-Bis (DIPHENYLPHOSPHINO) FERROCENE] DICHLOROPALLADIUM (II) (0. 03MOL%). The reaction mixture was heated at 160C for 2 X 600S. AFTER completion (monitored by LC- MS), the acetonitrile was evaporated to give A black solid. The solid was dissolved in EtOAc and washed with water, brine and dried over MgSO4. After filtration, the solvent was evaporated under vacuum. The solid material was then dissolved in chloroform and filtered through silica. The chloroform was evaporated to give A dark green solid (used as crude for the next reaction).

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2005/32493; (2005); A2;,
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Analyzing the synthesis route of 849758-12-9

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-bromo-3-fluorobenzoate

a- Synthesis of Int. 272: In a microwave vial, a mixture of methyl 4-bromo-3-fluorobenzoate (1.00 g 4.3 mmol), cyclopropylboronic acid (1.1 g, 13 mmol) and KF (0.75 g, 13 mmol) in dry toluene (10 mL) was purged with N2. Pd(PPh3)4 (0.25 g, 0.22 mmol) was added and the mixture was purged again with N2 and heated at 150C for 2h. The crude was partitioned between DCM and water. The organic layer was separated, dried over MgS04, filtered through a pad of silica gel and evaporated in vacuo to give 0.85 g of Int. 272 (quant.) which was used as such in the next reaction step.

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; PASQUIER, Elisabeth, Therese, Jeanne; DESCAMPS, Sophie; MERCEY, Guillaume, Jean, Maurice; WROBLOWSKI, Berthold; VIALARD, Jorge, Eduardo; MEERPOEL, Lieven; JEANTY, Matthieu, Ludovic; JOUSSEAUME, Thierry, Francois, Alain, Jean; WO2015/144799; (2015); A1;,
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Extended knowledge of Methyl 4-bromo-3-fluorobenzoate

According to the analysis of related databases, 849758-12-9, 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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6BrFO2

Step b) Methyl 4-acetoxy-3-fluorobenzoate (9b) Allyl chloride (105 muL, 1.28 mmol) and TFA (20 muL, 0.26 mmol) were added to a suspension of zinc dust (480 mg, 7.34 mmol) and anhydrous cobalt(II) bromide (96.6 mg, 0.44 mmol) in MeCN (4 mL), under inert gas. After stirring at room temperature for 10 min, the aryl bromide (1.003 g, 4.30 mmol dissolved in 5 mL MeCN) from (a) was added, followed by acetic anhydride (0.45 mL, 4.79 mmol) and more MeCN (1 mL). The mixture was stirred overnight, quenched with 1M HCl (20 mL), and then extracted with EtOAc (3*20 mL). The organic phase was washed successively with saturated aqueous NaHCO3 (20 mL) and saturated NaCl (2*20 mL), dried (Na2SO4), and concentrated. Flash chromatography (silica, 6/1 to 4/1 petroleum ether-EtOAc gave recovered bromide (161.1 mg, 16%) and the desired ketone (white solids, 305.5 mg, 36%). NMR (CDCl3) delta ppm: 1H (400 MHz) 7.94-7.86 (m, 2H), 7.80 (dd, 1H, J=11.2, 1.6 Hz), 3.95 (s, 3H), 2.67 (d, 3H, J=4.4 Hz); 19F (376 MHz)-109.2 (m); 13C (100 MHz) 195.4 (d, J=3.7 Hz), 165.1 (d, J=2.2 Hz), 161.6 (d, J=255 Hz), 135.8 (d, J=8.1 Hz), 130.7 (d, J=2.9 Hz), 129.0 (d, J=14 Hz), 125.2 (d, J=3.6 Hz), 117.9 (d, J=26 Hz), 52.7 (s), 31.4 (d, J=7.3 Hz).

According to the analysis of related databases, 849758-12-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nilsson, Magnus; Oden, Lourdes; Kahnberg, Pia; Grabowska, Urszula; US2009/23748; (2009); A1;,
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Introduction of a new synthetic route about C8H6BrFO2

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H6BrFO2

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H6BrFO2

(32d) methyl 4-acetyl-3-fluorobenzoate Cobalt (II) bromide (976 mg, 4.46 mmol) and zinc (4.96 g, 75.8 mmol) were suspended in acetonitrile (40 mL) and, under a nitrogen atmosphere, allyl chloride (1.10 mL, 13.4 mmol) and trifluoroacetic acid (0.205 mL, 2.68 mmol) were added, and the mixture was stirred for 10 min. A solution (60 mL) of methyl 4-bromo-3-fluorobenzoate (10.4 g, 44.6 mmol) produced in Example 32 (32c) and acetic anhydride (4.64 mL, 49.1 mmol) in acetonitrile was added, and the mixture was stirred at room temperature for 18 hr. To the reaction mixture was added 1.0 M hydrochloric acid (2.7 mL), and the mixture was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 10:1, V/V). The solvent of the object fraction was evaporated under reduced pressure to give the title object compound as a pale-yellow powder (1.78 g, yield 20%). 1H-NMR (CDCl3, 400 MH) delta: 2.68 (3H, d, J=4.6 Hz), 3.96 (3H, s), 7.77-7.95 (3H, m).

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; Kyoto Pharmaceutical Industries, Ltd.; SHIRAHASE, Hiroaki; TAKAHASHI, Kenji; SHOJI, Yoshimichi; TAKEDA, Shigemitsu; (111 pag.)US2016/207883; (2016); A1;,
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Share a compound : Methyl 4-bromo-3-fluorobenzoate

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-bromo-3-fluorobenzoate

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-bromo-3-fluorobenzoate

Step 1: methyl 4-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H- pyrrolo[2,3-d]pyrimidin-4-yl)-lH-pyrazol-l-yl]azetidin-l-yl}-3-fluorobenzoate2,2′-Bis(diphenylphosphino)-l,l’-binaphthyl (0.11 g, 0.18 mmol) was added to a mixture of {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3- d]pyrimidin-4-yl)-lH-pyrazol-l-yl]azetidin-3-yl}acetonitrile dihydrochloride (0.86 g, 1.8 mmol), methyl 4-bromo-3-fluorobenzoate (0.50 g, 2.1 mmol, Combi-Blocks: Cat.No.CA-4107), and cesium carbonate (1.7 g, 5.4 mmol) in toluene (25.0 mL) under N2, followed by palladium acetate (0.040 g, 0.18 mmol). The reaction mixture was stirred at 120C for 5 hours. The reaction mixture was diluted with ethyl acetate, filtered, and concentrated under reduced pressure to afford the desired crude product (1.06 g) which was directly used in next step reaction without furtherpurification. LCMS (M+H)+: m/z = 562.3.

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; INCYTE CORPORATION; YAO, Wenqing; BURNS, David M.; ZHUO, Jincong; WO2012/177606; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sources of common compounds: 849758-12-9

Application of 849758-12-9, A common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

Application of 849758-12-9, A common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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 solution of methyl 4-bromo-3-fluorobenzoate (526 mg, 2.26 mmol) in dioxane (10 mL) and H20 (2 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)- 1H-pyrazole- 1 -carboxylate (797 mg, 2.71 mmol), K3P04 (958 mg, 4.51 mmol) and XPhos-G2-Pd-preCat (35.5 mg, 0.045 mmol) at rt. The reaction was stirred under N2 at 60 C overnight. The reaction mixture was diluted with EtOAc,washed with H20 and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The crude product was purified by normal phase chromatography to give two products as white solids. Intermediate 151A (463 mg, 64%): ?H NMR (400MHz, CDC13) oe 8.51 (d,J=1.5 Hz, 1H), 8.10 (s, 1H), 7.84 (dd,J=8.1, 1.5 Hz, 1H), 7.79 (dd, J=11.4, 1.5 Hz, 1H), 7.63 (t,J=7.8 Hz, 1H), 3.92 (s, 3H), 1.68 (s, 9H). LC-MS(ESI) m/z:321.0 [M+H]. Intermediate 151B (175 mg, 35%): ?H NMR (400MHz, CDC13)oe 8.06(d, J=1.8 Hz, 2H), 7.85 (dd,J=8.1, 1.8 Hz, 1H), 7.80 (dd,J11.7, 1.5 Hz, 1H), 7.66 (t,J7.7 Hz, 1H), 3.94 (s, 3H). LC-MS(ESI) m/z: 221.0 [M+H].

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Ester – Wikipedia,
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Introduction of a new synthetic route about 849758-12-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 849758-12-9, its application will become more common.

Some common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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-bromo-3-fluorobenzoate

To a solution of 8 (1.5g, 7.69mmol) in 1,4-dioxane was added 2eq. l-methyl-3- trifluoromethylpyrazole-5-boronic acid, Pd(dppf)2C12 (0.5g) and 3eq.K3P04. 3H20. The reaction mixture was sparged with nitrogen for 10 minutes. And the resulting mixture was stirred at 85C for 15 hours under the N2. EA/brine work and followed by prep HPLC purification to give 1.3 g compound 9. l .lg of 10 was obtained after hydrolysis with aq. LiOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 849758-12-9, its application will become more common.

Reference:
Patent; CALCIMEDICA, INC.; WHITTEN, Jeffrey P.; PEI, Yazhong; CAO, Jianguo; WANG, Zhijun; ROGERS, Evan; DYCK, Brian; GREY, Jonathan; WO2011/139765; (2011); A2;,
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Simple exploration of 849758-12-9

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

Application of 849758-12-9, 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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 4-bromo-3-fluoro-benzoic acid methyl ester (1 g, 4.29 mmol), hydrazine hydrate (2.2 ml_, 42.9 mmol) and MeOH (20 ml_) was heated at 70 C for overnight. Concentrated, diluted with EtOAc (300 ml_) and washed with water (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated give the desired product 2AR (0.9 g, 90%).

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

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics