Category: 618-89-3

Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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 C8H7BrO2

In a 25 mL round-bottomed flask, toluene (10 mL) was degassed with argon for 20 min. Under a flow of argon, Pd(OAc)2 (0.05 g, 0.23 mmol), BINAP (0.23 g, 0.37 mmol) and Cs2CO3 (2.12 mmol, 6.51 mmol) were added and left to stir for a further 20 min. To the mixture, methyl (3-bromobenzoate) 1 (1.01 g, 4.65 mmol) and aniline 2 (0.51 mL, 5.58 mmol) were added. The reaction was stirred at 120 C and monitored by thin layer chromatography (TLC) for 24 h. Upon completion, the reaction was cooled to room temperature and filtered through Celite, with hexane as the eluent, followed by concentration under reduced pressure. The residue was purified by flash column chromatography on silica eluting with hexane/ethyl acetate (90:10) (Rf 0.23) to afford 0.87 g (82%) of 3 as a pale yellow solid; M.p. 110-112 C (literature M.p. 110-111 C) [40]; 1H NMR (400 MHz/CDCl3)/ppm, delta = 3.90 (s, 3H,-COOCH3), 5.81 (s, 1H, -NH), 6.98 (app. t, 1H, app J = 8 Hz, CHparaC4H4-NH), 7.09 (app. d, 2H, CHparaC2H2metaC2H2ortho-NH), 7.23 (m, 1H, HN-CH-C(COOCH3)-CHCHCH-), 7.29 (m, 3H, C2H2ortho-HN-CH-C(COOCH3)-CHCHCH-), 7.57 (app. d, 1H, HN-CH-C(COOCH3)-CH), 7.72 (m, 1H, HN-CHC(COOCH3)); 13C NMR (100 MHz/CDCl3)/ppm, delta = 52.2, 118.2, 118.4, 121.5, 121.77, 121.80, 129.4, 129.3, 131.4, 142.4, 143.6, 167.1; Found [M+H]+ (C14H14NO2) m/z 228.1019 (Calc. 228.1025); IR (ATR) v/cm-1: 3358, 3030, 1694, 1578, 1294, 744.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 618-89-3, its application will become more common.

Reference:
Article; Higgins, Clare L.; Filip, Sorin V.; Afsar, Ashfaq; Hayes, Wayne; Tetrahedron; vol. 75; 51; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 618-89-3, name is Methyl 3-bromobenzoate, 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 618-89-3, SDS of cas: 618-89-3

3-(3-bromophenyl)-3-oxopropanenitrile: Acetonitrile (21.86 mL, 419 mmol) was added to a stirred suspension of 60% NaH (7.25 g, 181 mmol) in THF (150 mL). Then, methyl 3-bromobenzoate (30 g, 140 mmol) was added and the mixture was heated at 75C for 4 h. After cooling to room temperature, water followed by iN HC1 (200 mL) was added and the mixture was extracted with ethyl acetate (500 mL), washed with sat .NaHCO3 solution (200 mL), dried (Na2SO4), filtered andconcentrated to afford 3-(3-bromophenyl)-3-oxopropanenitrile (29 g, 129 mmol, 93% yield) as light yellow solid. ?H NMR (500 MHz, CDC13) oe 8.09 (t, J1 .7 Hz, 1H),7.90 – 7.86 (m, 1H), 7.83 (ddd, J8.0, 2.0, 1.1 Hz, 1H), 7.45 (t, J7.9 Hz, 1H), 4.08(s, 2H).

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; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; PATEL, Manoj; D’ANDREA, Stanley; ZHENG, Zhizhen Barbara; CONNOLLY, Timothy P.; LANGLEY, David R.; PEESE, Kevin; WANG, Zhongyu; WALKER, Michael A.; KADOW, John F.; WO2015/126376; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 618-89-3,Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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.

2- (3-Bromo-phenyl)-propan-2-ol :; The 3-bromo-benzoic acid methyl ester (1.0 g, 4.7 mmol) in tetrahydrofuran (10 mL) was brought to-78 C followed by the addition of methyl magnesium bromide (7.7 mL, 10.81 mmol) and warmed to room temperature and stirred for 17 h. The mixture was poured into sat NH4Cl and extracted with ethylacetate. The organic extracts were combined, washed with brine, dried over magnesium sulfate and chromatographed on silica gel using 04% methanol/dichloromethane to afford colorless oil.

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-bromobenzoate, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2005/70932; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 618-89-3, name is Methyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 618-89-3

Methyl 3-bromobenzoate (110 g, 0.51 mol), dry acetonitrile (500 mL), ethynyl(trimethyl)silane (60.0 g, 0.61 mol), diisopropylamine (62.0 g, 0.61 mol) and tetra(triphenylphosphine)palladium (23.6 g, 0.02 mol) were placed under an atmosphere of argon in a three-necked round-bottomed 1 liter flask, equipped with a magnetic stirrer and a thermometer. The mixture was stirred for 30 minutes and then cooled to 10 0C. Copper iodide (9.7 g, 0.06 mol) was added, and the obtained suspension was stirred for a further 2.5 hours at 20 0C and finally for 3 hours at 60 0C. Then the mixture was left to stand at room temperature overnight and filtered. The precipitate of hydrobromide was washed with ether, and the combined filtrate was washed with saturated aqueous solutions of NH4CI and NaCI, dried over Na2SO4 and evaporated. The crude product was purified by chromatography (hexane) on a silica gel column to give methyl 3-(2- (trimethylsilyl)ethynyl)benzoate in 95% (112.8 g) yield.A suspension of methyl 3-(2-(trimethylsilyl)ethynyl)benzoate (112.8 g, 0.48 mol), mercury(2+) diacetate (16.2 g, 0.005 mol) in THF (350 mL) and concentrated H2SO4 (40 mL) was stirred at 60 0C for 3 hours. Then the mixture was cooled, diluted with ether (500 mL), filtered to remove precipitated mercury salts and washed to obtained neutral medium. Then the solution was dried over Na2SO4 and evaporated. The residue was purified by chromatography (hexane/ethyl acetate 4:1) on a silica gel column to give methyl 3-acetylbenzoate in 75% (65.2 g) yield.(Dimethoxymethyl)dimethylamine (90 mL) was added to a suspension of methyl 3-acetylbenzoate (65.2 g, 0.27 mol) in toluene (90 mL). The mixture was refluxed for 9 hours, during which time forming methanol was distilled off. The solution was then concentrated in vacuo, and the residue was purified from ether by crystallization to give methyl 3-(3-(dimethylamino)acryloyl)benzoate as yellow prismatic crystals in 80% (68.1 g) yield. ‘ . lmidoformamide acetate (20.3 g, 0.19 mol) was added to a suspension of methyl 3-(3- (dimethylamino)acryloyl)benzoate (30.3 g, 0.13 mol) in toluene (300 mL). The reaction mixture was refluxed for 20 hours, during which time toluene and dimethylamine acetate were distilled off* Then imidoformamide acetate (6.7 g) and toluene (175 mL) were added again, and after 8 hours the mixture was evaporated in vacuo. The residue was purified by chromatography (ethylacetate/hexane 3:1) on a silica gel column to afford methyl 3-(pyrimidin-4-yl)benzoate in 70% (19.5 g) yield.A suspension of methyl 3-(pyrimidin-4-yl)benzoate (19.5 g, 0.091 mol), sodium methylate (7.6 g, 0.14 mol) in ethanol (250 mL) was refluxed for 30 minutes. Then the reaction mixture was cooled, and the formed-precipitate was separated by filtration was dissolved in water. The obtained solution was acidified with concentrated HCI to pH about 2 that caused precipitation. The precipitate was separated by filtration, washed with water and dried to give the title compound as crystals in 94% (17.2 g) yield.

The synthetic route of 618-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65508; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 618-89-3,Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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 18(a)Methyl 3-{[5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-yl]amino}benzoate 5-Fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-amine (obtained from Example 1(b)) (99 mg, 0.42 mmol), methyl 3-bromobenzoate (97 mg, 0.45 mmol) and Cs2CO3 (230 mg, 0.71 mmol) were mixed in anhydrous 1,4-dioxane and the mixture was flushed with argon for 10 minutes before Pd2(dba)3 (23 mg, 0.025 mmol) and X-Phos (24 mg, 0.050 mmol) were added. The mixture was flushed with argon, then heated in a sealed tube at +90-100 C. until the reaction was complete. The reaction mixture was diluted with CH2Cl2, filtered and evaporated. The residue was taken up in CH2Cl2 and the organic phase was washed with H2O. Residual water was removed from the organic phase by treatment with Na2SO4. The crude of the base product was purified using preparative HPLC to give the title compound (97 mg, 62%) as a solid.1H NMR (400 MHz, DMSO-d6) delta ppm 9.73 (s, 1H) 8.57 (d, 1H) 8.19 (t, 1H) 8.04-7.95 (m, 1H) 7.59-7.52 (m, 1H) 7.43 (t, 1H) 7.37 (d, 1H) 5.44-5.31 (m, 1H) 3.84 (s, 3H) 2.51 (s, 3H) 1.42 (d, 3H) 1.40 (d, 3H); MS (ESI) m/z 370 (M+1).

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-bromobenzoate, its application will become more common.

Reference:
Patent; AstraZeneca AB; US2008/214560; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 618-89-3, 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 618-89-3 as follows.

General procedure: Under inert atmosphere (N2), in a 25 mL round bottom flask, Ar3Bi (0.208 mmol; 0.35 eq.), CsF (0.24 g: 1.8 mmol; 3 eq.), PPh3 (0.004 g: 0.018 mmol; 3 mol%), the aryl bromide (0.60 mmol; 1 eq.) was added to DMF (5 mL). The solution was warmed to 90 C prior addition of PEPPSI IPr (0.012 g: 0.018 mmol; 3 mol%). The reaction was monitored by GC/MS to follow the total consumption of the aryl bromide. Cooled to room temperature (RT), the reaction mixture was diluted by addition of diethyl ether (20 mL) and aqueous HCl 6 M (30 mL). After decantation, the aqueous solution was extracted with diethylether (2 * 20 mL). The collected organic phases were then washed with HCl 6 N (2 * 25 mL), water (25 mL) and brine (25 mL) prior drying over MgSO4. After concentration under reduced pressure, the resulting crude product was subjected to purification by column chromatography leading after concentration under reduced pressure to the title compound.

According to the analysis of related databases, 618-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cassirame, Benedicte; Condon, Sylvie; Pichon, Christophe; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 94 – 102;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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. Recommanded Product: Methyl 3-bromobenzoate

In a 25 mL round-bottomed flask, toluene (10 mL) was degassed with argon for 20 min. Under a flow of argon, Pd(OAc)2 (0.05 g, 0.23 mmol), BINAP (0.23 g, 0.37 mmol) and Cs2CO3 (2.12 mmol, 6.51 mmol) were added and left to stir for a further 20 min. To the mixture, methyl (3-bromobenzoate) 1 (1.01 g, 4.65 mmol) and aniline 2 (0.51 mL, 5.58 mmol) were added. The reaction was stirred at 120 C and monitored by thin layer chromatography (TLC) for 24 h. Upon completion, the reaction was cooled to room temperature and filtered through Celite, with hexane as the eluent, followed by concentration under reduced pressure. The residue was purified by flash column chromatography on silica eluting with hexane/ethyl acetate (90:10) (Rf 0.23) to afford 0.87 g (82%) of 3 as a pale yellow solid; M.p. 110-112 C (literature M.p. 110-111 C) [40]; 1H NMR (400 MHz/CDCl3)/ppm, delta = 3.90 (s, 3H,-COOCH3), 5.81 (s, 1H, -NH), 6.98 (app. t, 1H, app J = 8 Hz, CHparaC4H4-NH), 7.09 (app. d, 2H, CHparaC2H2metaC2H2ortho-NH), 7.23 (m, 1H, HN-CH-C(COOCH3)-CHCHCH-), 7.29 (m, 3H, C2H2ortho-HN-CH-C(COOCH3)-CHCHCH-), 7.57 (app. d, 1H, HN-CH-C(COOCH3)-CH), 7.72 (m, 1H, HN-CHC(COOCH3)); 13C NMR (100 MHz/CDCl3)/ppm, delta = 52.2, 118.2, 118.4, 121.5, 121.77, 121.80, 129.4, 129.3, 131.4, 142.4, 143.6, 167.1; Found [M+H]+ (C14H14NO2) m/z 228.1019 (Calc. 228.1025); IR (ATR) v/cm-1: 3358, 3030, 1694, 1578, 1294, 744.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 618-89-3, its application will become more common.

Reference:
Article; Higgins, Clare L.; Filip, Sorin V.; Afsar, Ashfaq; Hayes, Wayne; Tetrahedron; vol. 75; 51; (2019);,
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 618-89-3 as follows. Formula: C8H7BrO2

To a soiuiion of Compound 5-1 (2,00 g, 9.30 mmol, 1.00 eq) and morpholine (972 mg, 1 1.2 mmol, 1.20 eq) in toluene (20 n L) was added Cs2Ci (6.10 g, 1 8.6 mmol 2.00 eq), BINAP (289 mg, 465 umol, 0,05 eq) and Pd(OAe)2 (104 mg, 465 umo, 0.05 eq). The mixture stirred at 100 C in N2 atmosphere for 1 8 hr. The solid was filtered off and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (PE:EtOAc=10: 1 to 5: 1 ) to afford Compound 6-2 (1.40 g, 69% yield) as a colorless oil. ‘HNMR: (400 MHz, CDCb) delta 7.607 (s, 3H), 7.567 (d, J=8 Hz, IH), 7.357 ( =4 Hz, I H), 7.134-7.128 (m, 4H), 3.930 (s, 3H), 3.897 (t, J-4.8 Hz, 4H), 3.230 (t, J=4.8 Hz, 4H).

According to the analysis of related databases, 618-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF UTAH RESEARCH FOUNDATION; VANKAYALAPATI, Hariprasad; SHARMA, Sunil; LIU, Xiaohui; COBURN, Craig; (106 pag.)WO2017/4519; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 618-89-3, name is Methyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 3-bromobenzoate

I. Methyl 3-benzylbenzoate; [00306] A solution of 3-bromomethylbenzoate (500 mg, 2.18 mmol), phenylboronic acid (290 mg, 2.40 mmol), PdCl2(PPh3)2 (46 mg, 0.07 mmol) and K3PO4 (1.16 g, 5.45 mmol) in DMF (10 mL) and water (2 mL) was heated at 8O0C for 1 hr and then cooled to room temperature and diluted with EtOAc. The reaction mixture was washed with water (3 times) and saturated NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with 1 :19 EtOAc:hexanes to give a colorless oil (353 mg, 72%).

The synthetic route of 618-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENCYSIVE PHARMACEUTICALS, INC.; WO2008/79371; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 618-89-3, The chemical industry reduces the impact on the environment during synthesis 618-89-3, name is Methyl 3-bromobenzoate, I believe this compound will play a more active role in future production and life.

a. 3-Morpholin-4-yl-benzoic Acid Methyl Ester Following the procedure above except substituting “morpholine” for “pyrrolidine” and “methyl-3-bromobenzoate” for “methyl-4-bromobenzoate” gave the title compound: MS (M+H+): 222.

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 3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Quibell, Martin; Taylor, Steven; Grabowska, Urszula; Nilsson, Magnus; Morrison, Veronique; US2003/186962; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics