Category: 99548-54-6

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 99548-54-6 as follows. 99548-54-6

A solution of methyl 3-bromo-2-methylbenzoate (from for example AstaTech, 24.35 g, 106 mmol) in benzene (300 mL) was treated with N-bromosuccinimide (22.7 g, 128 mmol) followed by benzoyl peroxide, 95% (1.3 g, 5.35 mmol). The reaction mixture was flushed with nitrogen and kept under nitrogen. The reaction mixture was heated at 80C for 2 days. The reaction mixture was concentrated under reduced pressure and treated with hexanes (200 mL). The resulting solids were filtered off, washed with hexanes then with 25% EtOAc / hexanes. The filtrate was concentrated under reduced pressure and the residue was absorbed directly onto silica gel. The product was purified by chromatography (ISCOCombiflash, 330 g, 200 ml/min, 0-8.7% EtOAc / Hexanes over 30 minutes) to yield the title compound (32.4 g, 105 mmol, 99% yield) as an orange liquid. LC/MS: RT= 1.13 min, m/z = 226.8/228.9.

According to the analysis of related databases, 99548-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); A1;,
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Electric Literature of 99548-54-6,Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-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.

Example 110 methyl { (3S) -6- [ (3-bromo-2-methylbenzyl) amino] -2, 3-dihydro-l- benzofuran-3-yl } acetate; [0990][0991]Methyl 3-bromo-2-methylbenzoate (2.29 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 mL) , under ice-cooling, lithium aluminum hydride (0.285 g, 7.50 mmol) was added by small portions, and the mixture was stirred under a nitrogen atmosphere for 2 hr. Sodium sulfate 10 hydrate (2.42 g, 7.50 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized from heptane-ethyl acetate to give 3-bromo-2-methylbenzyl alcohol (1.76 g, yield 88%) as colorless crystals. This product (0.943 g, 4.69 mmol) was dissolved in acetonitrile (25 mL) , a Dess-Martin reagent (2.39 g, 5.63 mmol) was added by small portions under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was treated with saturated aqueous sodium hydrogen carbonate and aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A solution of the obtained colorless oil, methyl [ (3S) -6-amino-2, 3-dihydro-l- benzofuran-3-yl] acetate (0.972 g, 4.69 mmol) and acetic acid(0.537 mL, 9.38 mmol) in acetonitrile (25 mL) was stirred under a nitrogen atmosphere at room temperature for 0.5 hr. Sodium triacetoxyborohydride (1.99 g, 9.38 mmol) was added to the reaction mixture, and the mixture was further stirred for 12 hr. The reaction mixture was treated with water and saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate rhexane = 5:95-40:60) to give the title compound (1.59 g, yield 87%, 2 steps) as a colorless oil.1H NMR (300 MHz, CDCl3) delta 2.42 (3H, s) , 2.48-2.59 (IH, m) , 2.68-2.78 (IH, m) , 3.68-3.83 (4H, m) , 3.89 (IH, br s) , 4.18- 4.30 (3H, m) , 4.71 (IH, t, J = 9.1 Hz), 6.07-6.16 (2H, m) , 6.93 (IH, d, J = 8.0 Hz), 7.01 (IH, t, J = 7.9 Hz), 7.23-7.30(IH, m) , 7.49 (IH, dd, J = 7.9, 1.1 Hz). MS m/z 390 (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 3-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; NEGORO, Nobuyuki; TERAO, Yoshito; MIKAMI, Satoshi; YUKAWA, Tomoya; WO2010/143733; (2010); A1;,
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Application of 99548-54-6, These common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, 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: Aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3 (2.0 mmol), Pd(at)Al2O3-agarose (100 mg) and EtOH (5 mL) were added to a Schlenk flask. The mixture was stirred at room temperature under air. Upon complete consumption of starting materials as determined by TLC analysis, the solid was filtered and washed with acetone (3 × 5 mL). The combined organic solvents were concentrated in vacuum to afford product which was purified by silica gel column chromatography (petroleum ether/EtOAc = 10:1).

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Article; Wang, Peng; Cai, Jin; Chen, Junqing; Ji, Min; Journal of the Brazilian Chemical Society; vol. 26; 4; (2015); p. 748 – 754;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of Compound II (200 mg) and anisole (6.0 mL) were added phenylboronic acid (117 mg), PdCl2(dppf) (64 mg), potassium iodide (435 mg) and potassium carbonate (362 mg). The mixture was stirred at room temperature for 2.5 hours under carbon monoxide (1 atm) atmosphere, and then stirred at 100C overnight. The reaction mixture was diluted with ethyl acetate, and filtered through Celite. The filtrate was washed with brine, and the organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 100/0 to 85/15) to give Compound III (105 mg).

The synthetic route of Methyl 3-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; HORIUCHI, Yoshihiro; FUJIWARA, Hiroaki; SUDA, Hitoshi; SASAKI, Izumi; IWATA, Mitsutaka; SAWAMURA, Kiyoto; EP2612848; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a flask was added methyl 3-bromo-2-methylbenzoate (2 Ig, 91.7 mmol), potassium hexacyanoferrate (II) trihydrate (9.7g, 22.9 mmol), Na2Ctheta3 (9.7g, 91.7 mmol) and Pd(OAc)2 (102 mg) in N,N-dimethylacetamide (100 mL). The flask’s atmosphere was evacuated and replaced with nitrogen, and the reaction mixture heated at 1200C for 10 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (150 mL). The resultant slurry was filtered and washed thoroughly with ethyl acetate (2 x 50 mL). The combined filtrate was washed with brine and water, dried over Na2SO4 and evaporated under reduced pressure. The residue obtained after the concentration was purified using flash chromatography (ethyl acetate-hexanes (1:9) as the eluent) to provide methyl 3-cyano-2-methylbenzoate (11.2g, 70% yield). 1H NMR spectrum (in DMSO-d6): delta 8.03 (d, J= 8.1 Hz, IH); 7.98 (d, J= 7.9 Hz, IH); 7.49 (t, IH); 3.84 (s, 3H); 2.65 (s, 3H).

The synthetic route of Methyl 3-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INOTEK PHARMACEUTICALS CORPORATION; WO2008/106619; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, 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. Product Details of 99548-54-6

To a round-bottomed flask, methyl 3-bromo-2-methylbenzoate (18.3 g, 80 mmol, 1.0 eq), N-bromosuccinimide (17.1 g, 96 mmol, 1.2 eq) and benzoyl peroxide (1.9 g,8.0 mmol, 0.1 eq) were mixed in 150 mL of benzene. The reaction mixture was stirred at 80 C for 12 h. After cooling to room temperature, the reaction mixture was evaporated to remove most of the solvent. The resulting residue was purified by flash column chromatography with hexane/ethyl acetate to give the desired product Si as colorless oil (23.4 g, 95% yield).

The synthetic route of Methyl 3-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; HU, Yang; QIN, Chong; XU, Fuming; HU, Jiantao; XIANG, Weiguo; ZHOU, Bing; (233 pag.)WO2018/52949; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 99548-54-6, A common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-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 flask was added methyl 3-bromo-2-methylbenzoate (21 g, 91.7 mmol), potassium hexacyanoferrate (II) trihydrate (9.7 g, 22.9 mmol), Na2CO3 (9.7 g, 91.7 mmol) and Pd(OAc)2 (102 mg) in N,N-dimethylacetamide (100 mL). The flask’s atmosphere was evacuated and replaced with nitrogen, and the reaction mixture heated at 120 C. for 10 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (150 mL). The resultant slurry was filtered and washed thoroughly with ethyl acetate (2×50 mL). The combined filtrate was washed with brine and water, dried over Na2SO4 and evaporated under reduced pressure. The residue obtained after the concentration was purified using flash chromatography (ethyl acetate-hexanes (1:9) as the eluent) to provide methyl 3-cyano-2-methylbenzoate (11.2 g, 70% yield). 1H NMR spectrum (in DMSO-d6): delta 8.03 (d, J=8.1 Hz, 1H); 7.98 (d, J=7.9 Hz, 1H); 7.49 (t, 1H); 3.84 (s, 3H); 2.65 (s, 3H).

The synthetic route of 99548-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Inotek Pharmaceuticals Corporation; US2007/49555; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 99548-54-6, These common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, 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 3-bromo-2-methylbenzoate (10.0 g, 43.64 mmol, CAS : 99548-54-6) in benzene (60 ml) were added N-bromosuccinimide (6.1 g, 52.37 mmol) and benzoyl peroxide (1.05 g, 4.36 mmol) at rt. The reaction mixture was stirred at 80 C. for 12 h. The resulting reaction mixture was poured into EtOAc (260 mL) and the organic layer was washed with water (200 ml), separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue. The crude was purified by flash chromatography (eluting at 0-2% ethyl acetate in hexane) to afford 3-bromo-2-(bromomethyl) benzoate (12.0 g, 39.33 mmol). 1H NMR (400 MHz, DMSO-d6) delta 7.92 (dd, J=8.0, 1.3 Hz, 1H), 7.85 (dd, J=7.8, 1.3 Hz, 1H), 7.41 (t, J=7.9 Hz, 1H), 5.02 (s, 2H), 3.87 (s, 3H).

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: esters-buliding-blocks

Methyl 3-bromo-2-bromomethylbenzoate A mixture of methyl 3-bromo-2-methylbenzoate (17.0 g, 74.22 mmol) and N-bromosuccinimide (15.85 g, 89.06 mmol) in acetonitrile (200 mL) was heated under gently refluxing for 17 hours while a 200 W bulb situated 2 cm away was shining on the reaction flask. The mixture was cooled to room temperature and solvent was removed. The residue was dissolved in ethyl acetate (200 mL) and washed with water (3*80 mL), brine (80 mL) and dried (MgSO4). Solvent was removed to give methyl 3-bromo-2-bromomethylbenzoate (24.5 g, 97% by HPLC): 1H NMR (CDCl3) delta7.90-7.86 (dd, J=1.0 and 7.9 Hz, 1H), 7.78-7.74 (dd, J=1.2 and 8.2 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 5.12 (s, 2H), 3.95 (s, 3H).

The synthetic route of 99548-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Robarge, Michael J.; Chen, Roger Shen-Chu; Muller, George W.; Man, Hon-Wah; US2003/96841; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 99548-54-6, These common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, 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: Aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3 (2.0 mmol), Pd(at)Al2O3-agarose (100 mg) and EtOH (5 mL) were added to a Schlenk flask. The mixture was stirred at room temperature under air. Upon complete consumption of starting materials as determined by TLC analysis, the solid was filtered and washed with acetone (3 × 5 mL). The combined organic solvents were concentrated in vacuum to afford product which was purified by silica gel column chromatography (petroleum ether/EtOAc = 10:1).

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Article; Wang, Peng; Cai, Jin; Chen, Junqing; Ji, Min; Journal of the Brazilian Chemical Society; vol. 26; 4; (2015); p. 748 – 754;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics