Category: bromides-buliding-blocks

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. 4117-09-3, name is 7-Bromo-1-heptene, A new synthetic method of this compound is introduced below., Product Details of 4117-09-3

Mg shavings (939 mg, 38.6 mmol) are suspended in Et2O (20 ml)and 1-bromohept-6-ene (3.385 g, 19.115 mmol) is added dropwise. Thereaction mixture is stirred at RT for 3 h. Then the Grignard reagent isadded to EtOSiCl3 (945 mg, 5.150 mmol), dissolved in Et2O (20 ml), at 0 C via cannula. The reaction mixture is allowed to warm to RT andthen stirred for 2 h. Subsequently, 20 ml of the solvent are removed invacuo and 20 ml of hexanes are added to precipitate the salts formedduring the Grignard reaction. The reaction mixture is ffiltered throughcelite and the solvent removed in vacuo. The crude product is purifiedby column chromatography (SiO2, hexanes : ethylacetate=8 : 1) and 2 from the first fraction. The colorless liquid 2d (510 mg, 0.778 mmol) isisolated from the second fraction as the major product in 30% yield. Tris(hept-6-enyl)ethoxysilane 21H NMR (CDCl3, 499.7 MHz): X (ppm)=5.81 (ddt,3Jtrans(1H-1H)=16.9, 3 Hz, 3Jcis(1H-1H) =10.2 Hz, 3J(1H-1H) =6.7 Hz,3H, H6), 4.99 (ddt, 3Jtrans(1H-1H) =17.1 Hz, 2J(1H-1H) =2.1 Hz, 4J(1H-1H) =1.5 Hz, 3H, H7Z), 4.93 (ddt, 3Jcis(1H-1H) =10.2 Hz, 2J(1H-1H) =2.3 Hz, 4J(1H-1H) =1.1 Hz, 3H, H7E), 3.65 (q, 3J(1H-1H)=6.9 Hz, 2H, H8), 2.00-2.07 (m, 6H, H5), 1.30-1.41 (m, 18H, overlappingH2, H3, H4), 1.17 (t, 3J(1H-1H) =6.9 Hz, 2H, H9), 0.56-0.61(m, 6H, H1); 13C{1H} NMR (CDCl3, 125.7 MHz): X (ppm)=139.21(C6), 114.11 (C7), 58.37 (C8), 33.73 (C5*), 33.11 (C3*), 28.57 (C4),23.02 (C2), 18.65 (C9), 13.59 (C1), *assignments interchangeable; 29Si{1H} NMR (CDCl3, 79.4 MHz): X (ppm)=15.36 (s).Hexakis(hept-6-enyl)disiloxane 2d.1H NMR (CDCl3, 499.7 MHz): X (ppm)=5.81 (ddt, 3Jtrans(1H-1H)=16.9 Hz, 3Jcis(1H-1H) =10.2 Hz, 3J(1H-1H) =6.7 Hz, 6H, H6), 4.99(ddt, 3Jtrans(1H-1H) =17.1 Hz, 2J(1H-1H) =2.1 Hz, 4J(1H-1H) =1.5 Hz,6H, H7Z), 4.93 (ddt, 3Jcis(1H-1H) =10.2 Hz, 2J(1H-1H) =2.2 Hz, 4J(1H-1H) =1.2 Hz, 6H, H7E), 2.04 (dt, 3J(1H-1H) =6.7 Hz, 3J(1H-1H)=6.6 Hz, 12H, H5), 1.30-1.43 (m, 36H, overlapping H2, H3, H4), 0.56-0.61 (m, 12H, H1); 13C{1H} NMR (CDCl3, 125.7 MHz): X(ppm)=139.16 (C6), 114.15 (C7), 33.69 (C5*), 33.01 (C3*), 28.57(C4), 22.91 (C2), 14.99 (C1), *assignments interchangeable

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; Guenther; Reibenspies; Bluemel; Molecular catalysis; vol. 479; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, 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 59907-13-0, Computed Properties of C7H6BrF

[0314] To a solution of 7-isopropyl-2-methyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2- yl) -pyrazolo[l,5-a]pyrimidine-5-carboxylic acid ethyl ester (120 mg, 0.32 mmol) and 2- bromo-l-fluoro-3-methyl-benzene (60.8 mg, 0.322 mmol) in toluene (3 mL) were added Pd(PPh3)4 (37.2 mg, 0.032 mmol) and K3P04 (273.4 mg, 1.28 mmmol). The resulting mixture was bubbled with N2 for 5 mins and stirred at 130 C irridiated by microwave for 2 hrs. Then the reaction mixture was filtered, and the filtrate was concentrated in vacuum to give a residue, which was purified by a reversed-phase column (B from 5-95, A: H20, B: ACN) to afford 3-(2-fluoro-6-methyl-phenyl) -7-isopropyl-2-methyl-pyrazolo[l,5- a]pyrimidine-5-carboxylic acid ethyl ester (30.0 mg, yield: 26%) as a yellow solid. [0315] 1HNMR (400 MHz, CD3OD): delta = 7.46 (s, 1H), 7.37-7.31 (m, 1H), 7.18 (d, J = 7.6 Hz, 1H), 7.04 (t, J= 8.8 Hz, 1H), 4.44-4.39 (m, 2H), 3.96-3.92 (m, 1H), 2.37 (s, 3H), 2.14 (s, 3H), 1.51 (d, J= 6.8 Hz, 6H), 1.38 (t, J= 7.2 Hz, 3H). MS: m/z 356.2 (M+H+).

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, 2-Bromo-1-fluoro-3-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; SMITH, Layton H.; PINKERTON, Anthony B.; HERSHBERGER, Paul; MALONEY, Patrick; MCANALLY, Danielle; (167 pag.)WO2019/32720; (2019); 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. 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., Safety of 4,6-Dibromodibenzo[b,d]furan

A mixture of 13 g (40 mmol) of 4,6-dibromobenzofuran, 11.3 g (40 mmol) of bis(4-tert-butylphenyl)amine, 0.9 g (0.8 mmol) of Pd2(dba)3, 1.2 g (0.6 mmol) of tri-tert-butylphosphine, 5.0 g (52 mmol) of sodium tert-butoxide, and 150 ml of toluene was placed under nitrogen, and then heated and stirred at 70 C. for 24 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. The solution was extracted with 100 ml of ethyl acetate and 300 ml of water. The organic layer was dried with anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica to give product (16 g, 30.4 mmol, 76%).

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; LUMINESCENCE TECHNOLOGY CORPORATION; Yen, Feng-Wen; Chuang, Li-Chieh; Huang, Tsun-Yuan; (76 pag.)US2019/348609; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 18648-66-3,Some common heterocyclic compound, 18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene, molecular formula is C20H15Br, 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-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannan (0.81 g 2.66 mmol), 1-bromo-4-(2,2-diphenylvinyl)benzene (a compound of the Chemical Formula 2r) (1.7 g, 3.2 mmol), and Pd(PPh3)4 (0.15 g, 0.13 mmol) were dissolved in toluene (40 ml), and then refluxed under nitrogen atmosphere for 8 hours. Subsequently, an organic layer was extracted with methylene chloride and water and distilled, and column chromatography was performed (eluent-MC:Hx=1:4) to synthesize a compound of the Chemical Formula 4r.1H NMR (CDCl3): [ppm]=4.68 (s, 2H), 4.72 (s, 2H), 6.71 (s, 1H), 6.96 (s, 1H), 7.08 (s, 1H), 7.18 (m, 4H), 7.40 (m, 2H), 7.48 (m, 6H), 7.56 (d, 3JHH=8.8 Hz, 2H).

The synthetic route of 18648-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dongjin Semichem Co., Ltd.; US2011/94588; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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. Application In Synthesis of 1,4-Dibromo-2,5-difluorobenzene

1,4-Dibromo-2,5-difluorobenzene (51.2 g, 188 mmol) was dissolved in 1,2-diethoxyethane (400 ml), and a 2.5 M n-butyllithium/ hexane solution (76.0 ml, 190 mmol) was slowly added dropwise thereto at -78 C. in the presence of nitrogen gas. [0674] After the reaction solution was stirred at -78 C. for 30 minutes, dry ice was added thereto, followed by stirring for further 30 minutes. After the temperature was gradually raised to room temperature, water (200 ml) was added to the reaction liquid. The reaction liquid was diluted with ethyl acetate, and washed with a 10% aqueous sodium carbonate solution (200 ml¡Á2). Then, the obtained aqueous layers were combined, and made acidic by adjustment with 1 N hydrochloric acid. The precipitated yellow solid was filtered and dried to obtain the title compound (30.0 g, 67%). [0675] 1H NMR (DMSO-d6, 400 MHz): delta 7.90-7.87 (m, 1H), 7.79-7.75 (m, 1H).; MS (ESI) m/z 191 (M+H-44)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-51-5, its application will become more common.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature 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.

Step C: 4-Amino-N-(3-bromo-4-fluorophenyl)-N’-hydroxy-1,2,5-oxadiazole-3-carboximidamide (4) 4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (33.8 g, 208 mmol) was mixed with water (300 mL). At 60 C., 3-bromo-4-fluoroaniline (Sigma-Aldrich) (43.6 g, 229 mmol, 1.1 equiv.) was added to the suspension with stirring for 10 min. A solution of sodium bicarbonate (26.3 g, 313 mmol, 1.5 equiv.) in water (300 mL) was added over 15 min with stirring at 60 C. After stirring 20 min, LCMS indicated reaction completion. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate (2*300 mL). The combined ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to give the desired product (65 g, 99%) as an off-white solid, which was used in the subsequent reaction without further purification. C9H7BrFN5O2 (MW 316.09), LCMS (EI) m/e 316/318 (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; INCYTE CORPORATION; Tao, Ming; Frietze, William; Meloni, David J.; Weng, Lingkai; Zhou, Jiacheng; Pan, Yongchun; US2015/133674; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1193389-40-0, name is 1-(4-Bromophenyl)cyclobutanamine hydrochloride, belongs to bromides-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. Recommanded Product: 1193389-40-0

Intermediate AN-(1-(4-bromophenyl)cyclobutyl)-4-(difluoromethoxy)benzenesulfonamideTo a solution of 1-(4-bromophenyl)cyclobutanamine, HCl (845 mg, 3.22 mmol) in DMF (10 mL), was added diisopropylethylamine (1.69 mL, 9.66 mmol) and 4-(difluoromethoxy)benzene-1-sulfonyl chloride (0.529 mL, 3.22 mmol). The reaction mixture was then stirred at r.t., overnight. This mixture was then used, as is, in the following experiment.

The synthetic route of 1193389-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2011/207749; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 154264-95-6, name is 7-Bromo-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine, 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 154264-95-6, COA of Formula: C9H10BrNO

n-BuLi (5.79 ml, 14.47 mmol) was added to a stirred, cooled -78 C solution of 7-bromo-4-methyl-3,4-dihydro-2H-l,4-benzoxazine (Int-81a, 3 g, 13.15 mmol) in THF (24 ml). After stirring lh at -78 C for 1 hour., DMF (2.037 ml, 26.3 mmol) was added dropwise and the mixture allowed to warm slowly over 2 hours to room temperature. The reaction was quenched with aqueous ammonium chloride, and the product extracted into ethyl acetate. The organic phase was washed with brine, dried (NaiSC ), filtered and under reduced pressure to provide Int-81b (2.32 g, 13.09 mmol, 100 % yield) as a green solid.

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; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph A.; ROSENBLUM, Stuart B.; COBURN, Craig A.; SHANKAR, Bandarpalle, B.; ANILKUMAR, G., Nair; CHEN, Lei; DWYER, Michael, P.; JIANG, Yueheng; KEERTIKAR, Kartik, M.; LAVEY, Brian, J.; SELYUTIN, Oleg, B.; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; RIZVI, Razia; ZENG, Qingbei; WO2012/41014; (2012); 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. 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H8Br2

To a 13 ¡Á 150 mm test tube equipped with magnetic stir bar were added [RhCp*(CH3CN)3](SbF6)2 (6.6mg, 4 mol %), NaOAc (32.8mg, 0.4 mmol, 2 equiv) and 2a-2o (0.3 mmol, 1.5 equiv). The test tube was sealed with a rubber septum and removed from the glove-box. The solution of 1a-1r (0.2 mmol, 1 equiv)in EtOH (2 mL) was injected into the test tube via syringe. The reaction mixture was placed in a preheated oil bath (60 ) for 12 h. Then the reaction mixture was concentrated in vacuo, the residue was dissolved in methylene chloride and purified by column chromatography (silica gel, n-hexane/EtOAc =20/1). 1-Methyl-3,4-diphenylisoquinoline (3aa): The title compound was obtained as white crystal in 91% yield (54.2 mg). 1H NMR (400 MHz, CDCl3) delta 8.24 – 8.16(m, 1H), 7.66 (m, 1H), 7.63 – 7.55 (m, 2H), 7.41 – 7.28 (m, 5H), 7.26 – 7.12 (m,5H), 3.09 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 157.78, 149.37, 140.90, 137.56,136.06, 131.44, 130.32, 130.04, 129.29, 128.24, 127.66, 127.18, 127.01, 126.62,126.29, 126.19, 125.60, 22.73. HRMS (EI) calcd. for C22H17N: [M]+, 295.1361. Found: m/z 295.1358.

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; Chu, Benfa; Fang, Lili; Guo, Shan; Qi, Bing; Shi, Pengfei; Wang, Qi; Zhu, Jin; Tetrahedron Letters; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 69321-60-4, 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. 69321-60-4, name is 2,6-Dibromotoluene, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1,3-dibromo-2-methylbenzene (Combi Blocks catOT-1437: 339 mg, 1.356 mmol), tert-butyl 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole-5-carboxylate (200.0 mg, 0.452 mmol), sodium carbonate (96 mg, 0.904 mmol) and tetrakis(triphenylphosphine)palladium(0) (52.2 mg, 0.045 mmol) in dioxane (3.00 mL)/ water (1.0 mL) was heated at 90 C. overnight. The reaction was then cooled to room temperature, diluted with saturated aqueous NH4Cl, and extracted with EtOAc (3¡Á30 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel, eluting with 0-40% EtOAc/hexanes, to give the desired product (210 mg). LC-MS calculated for C24H26BrN2O2S (M+H)+: m/z=485.1/487.1; found 485.0/487.0.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dibromotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary