Tag: M.W=100-200

Application of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 solution of 3-bromo-4-fluoroaniline ( 1.000 g, 5.263 mmol), methyl 4-(bi momethyl)-3-fluoi benzoate ( 1.430 g, 5.789 mmol) and potassium carbonate ( 1.455 g, 10.525 mmol) in acetonitrile ( 10 mL) was stirred at the room temperature for 15 hr, filtered to remove solids, and concentrated under the reduced pressure to remove the solvents. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / hexane = 0 % to 10 %) to give methyl 4-(((3-bromo-4-fluorophenyl)amino)methyl)-3-fluorobenzoate as palw brown oil ( 1.104 g, 58.9 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

Example 1; Preparation of (1RS.2SR.6RS.7Sf?)-4-(4′-chloro-4-methylbiphen-3-yl)-10- oxatricyclof5.2.1.02’6ldec-8-ene-3.5-dione.; Step 1 : Preparation of 3-amino-4′-chloro-4-methylbiphenyl.; Tetrakis(triphenylphosphine)palladium (0) (3.7 g, 3 mmol) and 4-chlorophenylboronic acid (20.2 g, 0.13 mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1 ,2-dimethoxy- ethane (200 ml). After stirring the reaction mixture for 15 minutes at 20 0C, a solution of 20% aqueous sodium carbonate (300 ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 3-amino- 4′-chloro-4-methylbiphenyl.

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; SYNGENTA LIMITED; WO2009/19015; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1575-37-7, name is 4-Bromobenzene-1,2-diamine, belongs to bromides-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 1575-37-7, Application In Synthesis of 4-Bromobenzene-1,2-diamine

Example 248B 5-Bromo-1H-benzotriazole A mixture of Example 248A (262 mg; 1.4 mmol) in 10% H2SO4 (4 mL) was treated with NaNO2 (120 mg; 1.7 mmol) in water (1 mL), stirred for 30 min., diluted with water, and extracted with EtOAc. The extracts were rinsed with brine, dried (Na2SO4), concentrated and purified by flash chromatography (5% MeOH/CH2Cl2) to provide the desired product.

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; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H15Br

General procedure: To a solution ofsodium 4-hydroxynaphthalene-1-sulfonate (2.0 g, 8.12 mmol) inethanol (6 mL) was added water (6 mL), sodium hydroxide (813 mg,20.31 mmol) and bromoethane (1.33 g, 12.18 mmol). The mixture wasstirred at 80 C overnight in a seal tube. The mixture was cooled andwhite solid precipitated. The resulting precipitated solid was filteredand the filtercake was washed with dichloromethane to give 10a as awhite solid. (1.92 g, yield 86.2%).

According to the analysis of related databases, 1647-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

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. 452-62-0, name is 3-Bromo-4-fluorotoluene, A new synthetic method of this compound is introduced below., SDS of cas: 452-62-0

14a. (2-Fluoro-5methylphenyl)(6-(4-methylthiophenyl)(2H-benzo(d)1,3-dioxolen-5-yl))methan-1-ol To a solution of 3-bromo-4-fluorotoluene (0.7 mL, 5 mmol) in anhydrous THF (25 mL) at -78 C. under nitrogen atmosphere, a solution of t-BuLi in pentane (5.9 mL, 10 mmol) was added and the mixture stirred for 15 minutes. (color change observed). To this reaction mixture the product of Example 1b (1.34 g, 5 mmol), dissolved in anhydrous THF (20 mL), was added drop-wise and stirred at -78 C. for 15 minutes, then slowly allowed to warm to room temperature and stirred for 3 hours at room temperature. The reaction was then quenched with saturated aqueous ammonium chloride and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate was evaported under reduced pressure. Purification by flash column chromatography using 5% ethyl acetate in hexanes as the eluant gave the title compound as a white solid, (1.42 g, 74% yield), mp 110 C. 1H NMR (CDCl3, 300 MHz) delta 7.26-7.18 (m, 5H), 7.01-6.98 (m, 1H), 6.87 (s, 1H), 6.82-6.76 (s, 1H), 6.69 (s, 1H), 5.97 (s, 1H), 5.95 (s, 2H), 2.50 (s, 3H), 2.31 (s, 3H), 2.10 (s, 1H). 13C NMR (CDCl3, 75.45 MHz) delta 159.5, 156.3, 147.1, 146.8, 137.4, 137.3, 135.0, 133.4, 133.4, 130.2, 129.8, 129.3, 129.2, 128.0, 127.9, 126.2, 115.0, 114.8, 110.0, 107.5, 101.2, 67.2, 20.8, 15.8. LRMS (APIMS) m/z 782 (2M+NH4)+, 365 (M-OH)+.

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; Khanapure, Subhash P.; Garvey, David S.; Earl, Richard A.; Ezawa, Maiko; Fang, Xinqin; Gaston, Ricky D.; US2002/119977; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrFN

To a solution of 5-bromo-2-fluoroaniline (1 g, 5.26 mmol) in L/,L/?-dimethylformamide (10 ml), potassium iodide (2.18 g, 13.1 mmol), and sodium carbonate (1 .95 g, 18.4 mmol) were added and the reaction mixture was heated to 150 C. Then 1 -bromo-2-(2-bromoethoxy)ethane (1.34 g, 5.77 mmol) was added and heating was continued for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2 x 15 mL). The combined organic extracts were dried over Na2S04, filtered and concentrated under reduced pressure to yield the crude product. The crude material was purified by flash column chromatography using hexane/ ethyl acetate (80:20) to afford the title compound (0.8 g, 58%).1H-NMR (400 MHz, CDCI3) d = 7.03-7.04 (m, 2H), 6.90-6.92 (m, 1 H), 3.87-3.88 (m, 4H), 3.08-3.10 (m, 4H).

The synthetic route of 2924-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AC IMMUNE SA; NAMPALLY, Sreenivasachary; GABELLIERI, Emanuele; MOLETTE, Jerome; (0 pag.)WO2019/233883; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, 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. Quality Control of 1-Bromo-2,4-difluorobenzene

1-Bromo-2,4-difluoro-5-nitrobenzene: To a 0¡ã C. mixture of 1-bromo-2,4-difluorobenzene (20.0 g; 11.7 mL; 0.100 mol) and H2SO4 (76.8 mL) was added HNO3 (68.0 mL) over 45 min at such a rate that the internal temperature was <7¡ã C. The resulting mixture was stirred for 1 h at 0¡ã C., poured into ice water (400 mL), stirred vigorously for 2-3 min and extracted with CH2Cl2 (400 mL). The organic layers were washed with brine (1.x.500 mL), dried over Na2SO4, filtered and evaporated to give the product as a yellow oil (23.5 g, 95percent). 1H NMR (CDCl3) delta 8.39 (t, J=7.2 Hz, 1H), 7.14 (ddd, J=0.3, 7.8, 9.9 Hz, 1H). The synthetic route of 1-Bromo-2,4-difluorobenzene has been constantly updated, and we look forward to future research findings. Reference:
Patent; Marzabadi, Mohammad R.; Chen, Chien-An; Jiang, Yu; Lu, Kai; Andersen, Kim; US2006/79522; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1422-54-4, 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. 1422-54-4 name is 2-Bromo-6-fluorotoluene, 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.

00183] Active magnesium (10 mmol) was added in a RB containing dry TBF (10ml) and added a iittie iodine and stirred the reaction mixture and to this was added compound 1 (in 2 ml THFJsIowiy and stirred to generate the Grignard reagent. The reaction mixture was cooled to 0 “C and added compound 2 (in THF) drop wise and stirred the reaction mixture at it for 2h. After 2h the reaction mixture was quenched with saturated MH4CI soliition and extracted wit EtOAc. The organic layer washed with water, brine, dried over sodium sulphate and evaporated under reduced pressure to obtain compound 3,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-6-fluorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; KANDULA, mahesh; WO2013/24376; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 452-74-4, A common heterocyclic compound, 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, molecular formula is C7H6BrF, 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.

Example 1Preparation of 4-bromo-3-fluorobenzyl bromide (III)A solution of 4-bromo-3-fluorotoluene (21.5 g, 0.114 moles) in acetonitrile (200 ml) is added with N-bromosuccinimide, (NBS; 21.2 g, 0.119 moles). The mixture is refluxed, added with dibenzoyl peroxide (1.4 g, 0.004 moles), refluxed for 3 hour, then cooled at room temperature, and extracted with water. The aqueous phase is discarded, and the organic phase is washed with brine, dried over sodium sulphate, and concentrated under vacuum to give an oil (27.1 g, 90% yield).

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; Chiesi Farmaceutici S.p.A.; US2011/39934; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 compounds BB-1-4 (1.00 g, 5.26 mmol, 1.00 eq), BB-18-1 (587.38 mg, 6.84 mmol, 1.30 eq), potassium phosphate (3.91 g, 18.41 mmol, 3.50 eq), triphenylphosphine (137.96 mg, 526.00 umol, 0.10 eq), and palladium acetate (59.05 mg, 263.00 umol, 0.05 eq) were dissolved in toluene (24.00 mL) and water (2.00 mL), heated to 100 C. in nitrogen ambient and reacted for 16 hours. After being heated, the reaction solution gradually turned dark brown from brown. Complete reaction of raw materials was observed by LCMS monitoring and a target compound was generated. The reaction solution was cooled to 23 C., followed by addition of 20 mL of water, extraction with ethyl acetate (20 mL*3), drying over anhydrous sodium sulfate, and filtration. A filtrate was dried by rotary evaporation under reduced-pressure distillation, and purified by flash silica gel column chromatography (petroleum ether:ethyl acetate=10:1). The reaction succeeded, and a yellow liquid product BB-18 (790.00 mg, yield: 99.35%) was obtained. MS (ESI) m/z: 152 [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 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; SHANDONG LUYE PHARMACEUTICAL CO., LTD.; ZHANG, Yang; FU, Zhifei; LUO, Miaorong; LI, Jian; CHEN, Shuhui; (93 pag.)US2019/169140; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary