Category: 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. SDS of cas: 99548-54-6

[000576] Synthesis of 9: [000577] A mixture of 7 (228 mg, 1.0 mmol), 8 (288 mg, 1.4 mmol), Na2C03 (212 mg, 2 mmol) and Pd(PPh3)4 (115 mg, 0.10 mmol) in 2 mL of toluene, 2 mL of ethanol and 2 mL of water was stirred under N2 protection at 80 C for 17 hours concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1 : 50) to give 9 as white oil (260 mg, yield: 83.8%). LC-MS m/z: 311.1 [M+H]+. LC-MS Purity (214 nm): > 96%; tR = 2.256 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 99548-54-6, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; ERB, Michael; QI, Jun; (96 pag.)WO2016/196879; (2016); A1;,
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Application of 99548-54-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 99548-54-6 name is Methyl 3-bromo-2-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of compound 32-1 (7 g, 40 mmol), methyl 3-bromo-2-methylbenzoate (11 g, 48 mmol), K3P04 (25 g, 120 mmol), Pd2(dba)3 (915 mg, 1 mmol), X-phos (952 mg, 2 mmol) in 100 mL of dried toluene was heated under a N2 atmosphere at 100C for 18 h. Then water (200 mL) wasadded,and the mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by flash column chromatography on silica gel eluted with petroleum ether:ethyl acetate (3:1) to give 32-2. MS (ESI) m / e (M+H): 323.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; NARGUND, Ravi P.; BLIZZARD, Timothy A.; JOSIEN, Hubert; BIJU, Purakkattle; PLUMMER, Christopher W.; DANG, Qun; LI, Bing; LIN, Linus S.; CUI, Mingxiang; HU, Bin; HAO, Jinlai; CHEN, Zhengxia; WO2014/19186; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 99548-54-6, name is Methyl 3-bromo-2-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 99548-54-6, Safety of Methyl 3-bromo-2-methylbenzoate

Production Example 6 Under a nitrogen atmosphere, a mixture of methyl 3-bromo-2-methylbenzoate (53.00 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane (88.10 g), bistriphenylphosphine palladium(II) dichloride (8.12 g), triphenylphosphine (6.07 g), potassium acetate (68.10 g) and dioxane (530 ml) was stirred at 100C for 29 hours, and then cooled to room temperature. The obtained reaction mixture was filtrated over Celite and washed with ethyl acetate. The obtained filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 54.00 g of methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzoate.

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-bromo-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Astellas Pharma Inc.; EP2216330; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of methyl 3-bromo-2-methylbenzoate (500 mg, 3.3 mmol), NBS (770.4 mg, 4.3 mmol), and di-benzoyl peroxide (BPO, 80.7 mg, 0.3 mmol) in 1,2-dichloroethane (10 mL) was heated at 80 C for 12 h. The reaction mixture was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over NaSO4, filtered and concentrated to give a crude product (683.2 mg, 89.6%), which was used in the next step reaction without further purification.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Qing; Meng, Liuwei; Zhou, Siru; Deng, Xiaoyan; Wang, Na; Ji, Yi; Peng, Yichun; Xing, Junhao; Yao, Gongmei; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 509 – 523;,
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Application 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.

Compound I-1B (4.56 g, 20 mmol) was dissolved in anhydrous THF (100 mL).After cooling to 0 C, LAH (0.8 g, 20 mmol) was added in portions to maintain the internal temperature of the reaction solution less than 5 C. After the addition, the temperature was slowly raised to room temperature for 2 hours.TLC showed that after the reaction was over, it was re-cooled to 0 C, 0.8 ml of water was added dropwise, 0.8 ml of 15% NaOH and 2.4 ml of water were added, and after stirring, the mixture was stirred for 1 hour and filtered.The obtained filtrate was dried to give Compound I-1C (3.7 g, yellow solid).Yield: 92.4%.

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; Guangzhou Dankang Pharmaceutical Biological Co., Ltd.; Xu Yong; Huang Lu; Lin Dang; Hu Hai; (29 pag.)CN110092740; (2019); A;,
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.

EXAMPLE 106A Methyl 6-amino-3-bromo-2-methylbenzoate A -20 C. solution of methyl 3-bromo-2-methylbenzoate (10 g, 43.7 mmol) in concentrated H2SO4 (100 mL) was treated dropwise with a solution of concentrated HNO3 (2.75 muL) in concentrated H2SO4 (50 mL) at a rate that maintained the temperature below -15 C. The reaction was then stirred at 0 C. for 30 minutes, poured into ice, and extracted with diethyl ether. The extract was washed with aqueous NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to give 9.32 g of the nitrated product. The crude product was added to a solution of SnCl2 (32.2 g, 170 mmol) in concentrated HCl (34 mL) and methanol (52 mL) and the resulting suspension was stirred at room temperature for 4 hours. The resulting solution was concentrated, adjusted to pH 7 with aqueous NaOH, and filtered through diatomaceous earth (Celite). The pad was washed with diethyl ether and dichloromethane and the combined filtrates were concentrated. The concentrate was purified by silica gel chromatography with 10-20% ethyl acetate/hexanes to give 3.59 g of the desired product. MS (ESI(-)) m/e 243 (M-H)-.

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

Reference:
Patent; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products 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;,
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. 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. Product Details of 99548-54-6

A mixture of 3-Bromo-2-methyl benzoic acid methyl ester (2.4 g, 10.29 mmol), NBS (1.83 g, 10.29 [MMOL)] and AIBN (4 mg) in [CHLOROBENZENE] (40 mi) was heated to [80C] under nitrogen for 18 hours. The mixture was cooled in an ice-bath, filtered and the solvent removed by evaporation under reduced pressure. The orange residue was purified by flash chromatography on silica gel eluting with a solvent gradient of heptane: ethyl acetate (40: 1) to give the title compound (2.74 g, 86 %) as a colourless oil. [1H-NMR] (400 MHz, [CDCI3)] : [ES] = 3.88 (s, 3H), 5.06 (s, 2H), 7.22 (dd, 1H), 7.68 (d, [1H),] 7. 89 (d, [1 H).] Microanalysis : Found: C, 35.21 ; H, 2.67 ; N, 0.00. [C9H8BR202] requires C, 35.10 ; H, 2.62 ; N, 0.00%.

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

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/14357; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 99548-54-6

< Step 2>; Methyl 3-bromo-2-methylbenzoate (4.67 g, 20 mmol) obtained in Step 1 and 100 mi of benzene were placed into a flask, and N-bromosuccinimide (4.37 g, 25 mmol) and 2,2′-azobisisobutylnitrile (0.336 g, 2 mmol) were added thereto. The resulting mixture was refluxed for 6 hours, cooled to 0 C , and filtered to remove precipitate. The resulting solution was washed successively with 10% sodium sulfite and saturated sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was removed under a reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain methyl 3- bromo-2-(bromomethyl)benzoate (5.27 g (84%)).1H nuMR (300 MHz, CDCl3) delta 7.62 (d, IH, J = 7.9 Hz), 7.49 (dd, IH, J = 7.9, 0.9 Hz), 6.99 (t, IH, J= 7.9 Hz), 4.88 (s, 2H), 3.70 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/51417; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

99548-54-6, Name is Methyl 3-bromo-2-methylbenzoate, 99548-54-6, 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.

Preparation Example 13 Under a nitrogen atmosphere, a mixture of methyl 3-bromo-2-methylbenzoate (53.00 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (88.10 g), bistriphenylphosphine palladium chloride (8.12 g), triphenylphosphine (6.07 g), potassium acetate (68.10 g), and dioxane (530 mL) was heated and stirred at 100 C. for 29 hours, and then cooled to room temperature. The reaction mixture was filtered through Celite and washed with ethyl acetate. The resulting filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (54.00 g) as a colorless oil.

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; Negoro, Kenji; Ohnuki, Kei; Yonetoku, Yasuhiro; Kuramoto, Kazuyuki; Urano, Yasuharu; Watanabe, Hideyuki; US2012/35196; (2012); A1;,
Ester – Wikipedia,
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