Category: bromides-buliding-blocks

Reference of 5003-71-4, 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. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-bromopropylamine hydrobromide (1.0 g, 4.6 mmol) in a 2:1 dioxane/H2O (45 mL) was cooled to 0 C. and treated with K2CO3 (6.22 g, 45 mmol) and di-tert-butyl dicarbonate (1.5 g, 6.9 mmol). The reaction was stirred for 15 h while warming to room temperature. The dioxane was removed in vacuo and the remaining aqueous mixture was acidified with 5 N HCl and extracted with ethyl acetate (5*25 mL). The combined organic layers were dried with MgSO4 and yielded 3-bromo-N-(tert-butoxycarbonyl)propylamine as a colorless oil (0.93 g, 93%). 1H-NMR (CDCl3/TMS, ppm): 1.41 (s 9H, CH3), 2.02 (quintet, J=6.4 Hz, 2H, CH2), 3.23 (m, 2H, NCH2), 3.41 (t, J=6.6 Hz, CH2Br), 4.8 (broad, 1H, NH); 13C-NMR (CDCl3, ppm): 28.3 (CH3), 30.7, 32.6, 38.9 (CH2), 79.3 (quaternary C), 155.9 (CO); MS (CI, m/z): 239, 241 (M+H+ Calc. for C8H16BrNO2 237.03644).

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, 3-Bromopropan-1-amine hydrobromide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Research Development Foundation; US6703384; (2004); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

[000821j To a stirred solution of compound 1 (2 g, 1 eq) in THF (40 mL), CDI (2.42 g, 1.5 eq) was added and heated to reflux for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate (100 mL) and washed with water. Organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the crude compound 2. LCMS (mlz): 226.90 (M + 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 556-96-7, 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. 556-96-7 name is 1-Bromo-3,5-dimethylbenzene, 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.

I.2 Synthesis Methods and Characterization of the CompoundsI2.1 Bis(3,5-Dimethylphenyl)Phosphinic Acid 1-Bromo-3,5-dimethylbenzene (13.63 g, 71.44 mmol, 97%) is added dropwise at room temperature to magnesium turnings (1.74 g, 71.44 mmol) in anhydrous THF (80 mL). Once the magnesium has dissolved completely, a solution of N,N-dimethylphosphoryl dichloride N(Me)2P(O)Cl2 (4.33 mL, 35.72 mmol) in anhydrous THF (10 mL) is added dropwise. To remove the salt formed in the reaction, the reaction mixture, after two hours, is added to an ice-cooled ammonium chloride solution (30 g in 500 mL of water). In a distillation apparatus, the THF is subsequently removed and the residue is boiled with concentrated HCl (75 mL) at 80 C. The resulting white solid is dissolved in aqueous NaOH (5.4 g, 300 mL of water) and the aqueous phase is extracted twice with diethyl ether. The clear aqueous phase is acidified again by adding concentrated HCl, in order to precipitate the phosphinic acid as a white solid in 70% yield (6.81 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3,5-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; KONINKLIJKE PHILIPS ELECTRONICS N.V.; OSRAM OPTO SEMICONDUCTORS GMBH; US2011/172423; (2011); 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Product Details of 1435-51-4

A solution of 28 (15.6 g, 0.05 mol) in Et2O (30 mL) was added dropwise at -78 C to a stirred solution of LDA, freshly prepared from diisopropylamine (5.5 g, 0.55 mol) and nBuLi (10 M, 5 mL, 0.05 mol) in THF (80 mL). After ca 30 min stirring at ca -78 C chlorodimethylsilane (5.0 g, 0.053 mol) was added slowly. The mixture was stirred for 30 min at -78 C and then was allowed to warm warm to ca. -50 C. 1 M aqueous H2SO4 (30 mL) was added with stirring. The organic phase was separated. The water phase was washed with Et2O (2 × 30 mL). The combined organic phase was dried over anhydrous MgSO4. It was filtered and evaporated under reduced pressure and the residue was subjected to a fractional distillation under reduced pressure. The crude product was obtained as a colorless liquid, b.p. 95-103 C (1 Tr). It tends to solidify partly when stored for a longer time at room temperature. Subsequent crystallization of this material from cold methanol (50 mL, -30 C) afforded pure product as a white solid, m.p. 28-30 C. Yield 13.5 g (73%). 1H NMR (400 MHz, CDCl3): delta 7.59 (s, 1H, Ph), 4.80-4.63 (m, 2H, SiH), 0.44 (dd, J = 3.9, 1.9 Hz, 12H, SiMe2) ppm. 13C NMR (101 MHz, CDCl3): delta 170.85 (d, J = 244.5 Hz), 132.84 (d, J = 3.5 Hz), 132.18 (d, J = 14.4 Hz), 124.42 (d, J = 38.8 Hz), -3.23 (d, J = 4.4 Hz) ppm. 19F NMR (376 MHz, CDCl3): delta -77.55 (m) ppm. Anal. Calcd for C10H15Br2FSi2 (370.20): C, 32.44; H, 4.08. Found: C, 32.23; H, 3.93.

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:
Article; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 445-02-3, A common heterocyclic compound, 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

Step A4-bromo-2-chloro-6-(trifluoromethyl)aniline[00296] 4-bromo-2-(trifluoromethyl)aniline (12.2 g, 50.8 mmol) was dissolved in acetonitrile (200 mL) before N-chlorosuccinimide (7.47 g, 55.9 mmol) was added and the mixture heated to 80 C. The reaction was stirred for 2 hours and allowed to cool to room temperature. The reaction mixture was quenched with water and extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue passed through a silica plug eluting with dichloromethane. The filtrate was concentrated to give the title compound (13.1 g, 94%) as a liquid. H NMR (400 MHz, DMSO- /6) delta ppm 7.78 (d, 1 H), 7.52 (d, 1 H), 5.92 (s, 2 H).

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; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John G; FANG, Jing; PEAT, Andrew James; TAI, Vincent; TURNER, Elizabeth; WO2011/97491; (2011); 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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Product Details of 1003-98-1

2-Bromo-4-fluoroaniline (0.54 g, 2.84 mmol) was dissolved in MeCN (14.21 ml). Ammonium thiocyanate (0.324 g, 4.26 mmol) was added to the reaction mixture followed by benzyltrimethylammonium tribromide (1.108 g, 2.84 mmol), and thereaction mixture was allowed to stir for 12 hours. The reaction mixture was diluted with saturated aqueous NaHCO3, and the solids were collected by suction filtration and washed with water to yield Intermediate 806A (0.700 g, 2.84 mmol, 100%). ?H NIVIR (4001V11{z, MeOH4) 7.41 (dd, J8.0, 2.5 Hz, 1H), 7.26 (dd, J8.9, 2.5 Hz, 1H). LC-MS. method H, RT = 0.81 mm, MS (ESI) m/z: 247/249 (M+H).

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; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1337523-99-5, A common heterocyclic compound, 1337523-99-5, name is 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine, molecular formula is C10H12BrN, 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.

In a 50-mL round-bottom flask, to a solution of 6-bromo-l ,2,3,4-tetrahydronaphthalen-l -amine (4.34 g, 19.17 mmol, 1.00 equiv) and TEA (3.07 g, 30.33 mmol, 1.58 equiv) in dichloromethane (80 mL) was added (Boc)20 (6.65 g, 30.47 mmol, 1.59 equiv) at 0 C. The resulting solution was stirred for 16 h at 25 C. After the reaction was done, it was quenched by the addition of water (10 mL) and the mixture was extracted with dichloromethane (3 x 20 mL). The combined organic layers were washed by brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with dichloromethane in petroleum ether (5% to 20% gradient) to afford tert-butyl N-(6-bromo-l, 2,3,4- tetrahydronaphthalen-l -yl)carbamate as white oil (6.2g, 95% for two steps). MS: m/z = 269.9[M+H-56]-

The synthetic route of 1337523-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; CALDWELL, Richard; LIU-BUJALSKI, Lesley; POTNICK, Justin; NEAGU, Constantin; KULKARNI, Shashank; JONES, Reinaldo; QIU, Hui; (238 pag.)WO2020/43638; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

At -40C,Add 2.0 M isopropyl chloride to a solution of 2-bromo-1,4-difluorobenzene (186 g) in THF (1.0 L)Magnesium in THF (482 mL),And continue stirring at 5 C for 1 h.At -40C,A solution of tert-butyl 2-oxopyrrolidine-1-carboxylate (215.5 g) in THF (250 mL) was added dropwise to the above reaction mixture.And continue stirring at 10 C for 2 h.The reaction mixture was quenched with saturated ammonium chloride solution,Extract with ethyl acetate,Dry with anhydrous sodium sulfatefilter,And concentrate the filtrate under reduced pressure,The crude title compound was obtained (323.4 g),It is used directly in the next step without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhu Li; Hu Yuandong; Dai Liguang; Yang Yanqing; Duan Xiaowei; Yang Zhao; Wu Wei; Sun Yinghui; Han Yongxin; Peng Yong; Luo Huiyan; Luo Hong; Yang Ling; Xu Hongjiang; Guo Meng; Zhong Zhaobo; Wang Shanchun; (102 pag.)CN108003161; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 61326-44-1, name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene, 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 61326-44-1, Product Details of 61326-44-1

Under argon protection,Tetrakis(4-bromophenyl)ethene 210.7 mg, 0.33 mmol) was added to the reaction flask in that order.3,4,5-trifluorobenzeneboronic acid (274.9 mg, 1.56 mmol),Potassium carbonate (135.4 mg, 0.98 mmol),Tetrakis(triphenylphosphine)palladium (20.3 mg, 0.018 mmol),Tetrabutylammonium bromide (12.3 mg, 0.038 mmol),Add 20 mL of toluene and 5 mL of deionized water.The mixture was heated to 100 ° C, reacted for 27 h, and the reaction was monitored by thin layer chromatography.After the system was lowered to 27 ° C, the liquid was separated.The aqueous phase was extracted with dichloromethane (15 mL×3) and the organic phases were combined.Add anhydrous sodium sulfate and filter,The filtrate is concentrated and subjected to thin layer chromatography.The developing agent ratio is dichloromethane: n-hexane (V: V) = 2:1,The bright blue band of the product (observed under a 365 nm UV lamp) is scraped off.After fully crushing, pour into a sand core funnel and rinse with 80 mL of dichloromethane.Evaporate dry solvent,Obtaining a yellow solid is the target product F-TPE,The weight was 169.2 mg, and the yield was 61.02percent.

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, 1,1,2,2-Tetrakis(4-bromophenyl)ethene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; University of Jinan; Miao Jinling; Xiong Zhixin; Nie Yong; Zhang Hao; (15 pag.)CN108947766; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5469-19-2, 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. 5469-19-2 name is 1-Bromo-2,4,5-trimethylbenzene, 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.

i 2,4,5-Trimethylbenzoic acid n-Butyllithium (100 ml of a 2.5M solution in hexanes) was added to a solution of 5-bromo-1,2,4-trimethylbenzene (50 g) in tetrahydrofuran (600 ml) at -70 C. After 1.5 hours the solution was warmed to -40 C. then cooled to -70 C. Carbon dioxide gas was bubbled through the solution for 10 minutes and the mixture was allowed to warm to room temperature. The solvent was evaporated and the residue partitioned between water and isohexane. The aqeous layer was acidified to pH 1 and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure. Yield 36.7 g. 1H NMR: delta (CDCl3) 7.85(s, 1H), 7.04(s, 1H), 2.59(s, 3H), 2.28(s, 3H), 2.27(s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,4,5-trimethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca U.K. Limited; US6162808; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary