Category: bromides-buliding-blocks

Application of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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: 4-(trans-4-pentyl-cyclohexyl)phenol (3.00 g, 12.2mmol), 5-bromo-1-pentene (2.18 g,14.6mmol), potassium carbonate (3.37 g, 24.2mmol) weremixed in N,N-dimethylformamide (30ml). The reaction mixturewas stirred and allowed to react at 80 C for 8 h. The crudeproduct was washed with water and a saturated aqueous sodiumchloride solution and extracted with ethyl acetate. The productwas purified by silica gel chromatography (eluent: hexane).Compound 3(3) was obtained with 39% yield (1.49 g, 4.74mmol). 1HNMR (400 MHz, CDCl3, ): 7.11 (2H, d, J = 8.3Hz), 6.82 (2H, d, J = 8.8 Hz), 5.905.80(1H, m), 5.064.99(2H, m), 3.94 (2H, t, J = 6.3 Hz), 2.40 (1H, tt, J = 12.2, 3.2Hz), 2.23 (2H, q, J = 7.3 Hz), 1.87 (6H, m), 1.451.20(11H,m), 1.03 (2H, dd, J = 24.2, 13.2), 0.89 (3H, t, J = 6.8 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-1-octene, its application will become more common.

Reference:
Article; Mizumura, Yurika; Hoegberg, Daniel; Arai, Kenichiro; Sakuda, Junji; Soberats, Bartolome; Yoshio, Masafumi; Kato, Takashi; Bulletin of the Chemical Society of Japan; vol. 92; 7; (2019); p. 1226 – 1233;,
Bromide – Wikipedia,
bromide – Wiktionary

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 58534-95-5 as follows. Computed Properties of C6H5BrFN

Step 4: N-(3-bromo-2-fluoroph pane-l-sulfonamideTo a stirred solution of 3-bromo-2-fluoroaniline (3 g, 0.0158 mol) in dichloromethane (300 mL) were added dropwise pyridine (12.53 mL, 0.158 mol) and 3-fluoropropane-l-sulfonyl chloride (7.64 mL, 0.047 mol) at 0C. To the resulting mixture was added DMAP (0.387 g, 0.00317 mol) at 0C. The reaction mixture was stirred overnight at room temperature. Water (500 mL) was added and the reaction mixture was extracted with DCM (2×100 mL). The combined organic layers were washed with IN HCI (50 mL) followed by brine and dried over anhydrous sodium sulfate, then filtered. The filtrate was evaporated under reduced pressure and the crude product was purified using column chromatography (100-200 mesh silica gel, 10% EtOAc in hexane) to afford the title compound (3.4 g, 69%). *H NMR (400 MHz, DMSO-d6) : delta 9.99 (s, 1H), 7.54 (t, J = 7.6 Hz, 1H), 7.42 (t, J = 8.4 Hz, 1H), 7.16 (t, J = 8.4 Hz, 1H), 4.61 (t, J = 3.2 Hz, 1H), 4.49 (t, J = 4.0 Hz, 1H), 3.25 (t, J = 5.6 Hz, 2H), 2.16-2.03 (m, 2H) ; ESI-MS : Calculated mass: 312.96; Observed mass: 314.0 [M+H]+.

According to the analysis of related databases, 58534-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; SMITH, Roger, A.; REDDY, Sanjeeva; JOHN, Tyler, M.; NYAVANANDI, Vijay, Kumar; SUBRAMANYA, Hosahalli; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; NADIPALLI, Prabhakara, Rao; SENGUPTA, Saumitra; WO2014/169167; (2014); A1;,
Bromide – Wikipedia,
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Reference of 67567-26-4,Some common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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 1-tert-butoxycarbonyl-4-methyl-piperidine-4-carboxylic acid (240 mg, 0.99 mmol, 1.0 eq.) in CH2Cl2 (8.0 mL) was added pyridine (320 mg, 0.32 mL, 3.9 mmol, 4.0 eq.), (COCl)2 (130 mg, 0.088 mL, 0.99 mmol, 1.0 eq.) followed by 2 drops of DMF. After 1 h at room temperature, 4-bromo-2,6-difluoro-aniline (210 mg, 0.99 mmol, 1.0 eq.) was added and the mixture was stirred at room temperature overnight, after which CH2Cl2 was added and washed with water and brine. The organic layers were dried, evaporated and purified over silica gel with ethyl acetate in hexanes (5 to 50% gradient) to give tert-butyl 4-[(4-bromo-2,6-difluoro- phenyl)carbamoyl]-4-methyl-piperidine-1-carboxylate (350 mg, 82%). 1H NMR (CDCl3) d: 7.43 (s, 1H), 7.11 (d, J= 6.6 Hz, 2H), 3.65 – 3.81 (m, 2H), 3.14 – 3.22 (m, 2H), 2.09 (d, J= 13.9 Hz, 2H), 1.46 – 1.52 (m, 2H), 1.45 (s, 9H), 1.32 (s, 3H).

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); 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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8BrN

Example 1.Preparation of 2-methyl-5-bromophenylguanidine nitrate of the Formula 3; Preparation of 5-bromo-2-methylaniline hydrochlorideA 5-L reactor has been charged with 812.3 g of 5-bromo-2-methylaniline (4.36 mol. 1.0 eq), and 3.7 kg of methylene chloride. After cooling the obtained clear solution to 1O0C, 190.7 g of dry hydrogen chloride gas was added from a bottle over a period of 2.5 h. The resulting mixture was stirred for ca. 30 minutes, whereafter the obtained crystalline product was filtered off on a filter funnel. The precipitate was washed on a filter funnel with two portions of methylene chloride (200 g each). The product was dried at room temperature for 3 days to yield 976.4 g of 5-bromo-2-methylaniline hydrochloride (100%) having an HPLC purity of 99.6%.

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; TEMAPHARM SP. z o.o.; GRUZA, Henryk; MIREK, Slawomir; JEZEWSKI, Artur; WRZOSEK, Artur; WO2010/14022; (2010); 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. 583-70-0, name is 2,4-Dimethylbromobenzene, A new synthetic method of this compound is introduced below., Formula: C8H9Br

General procedure: A flask furnishedwith a dropping funnel was charged with the aryl/alkylbromide in Et2O. n-BuLi(1.6 M in hexane) diluted with Et2O was added dropwise at -78C. After addition, thereaction was kept at -78C for 10 min and was then allowed to warm to room temperatureand stirred for 30 min. The solution was transferred via cannula to SiCl4 dissolved in Et2Oat 0C. The reaction was stirred for 2 h and was allowed to warm to room temperature. Thesolvent was removed under reduced pressure and the residue dissolved in boiling toluene.Insoluble salts were removed via filtration through cellite and washed with hot toluene. Thesolvent from the resulting clear solution was removed under reduced pressure, followed bypurification via distillation or recrystallization.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Binder, Judith; Fischer, Roland C.; Flock, Michaela; Torvisco, Ana; Uhlig, Frank; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; 11; (2015); p. 1980 – 1994;,
Bromide – Wikipedia,
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38573-88-5, name is 1-Bromo-2,3-difluorobenzene, 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. Application In Synthesis of 1-Bromo-2,3-difluorobenzene

General procedure: In a 15 mL sealed tube equipped with a magnetic stirring bar were added 1 (1 mmol),2 (0.8 mmol), tert-butyl isocyanide (1.2 mmol, 136 muL), Pd(OAc)2 (0.03 mmol, 7 mg),DPEPhos (0.06 mmol, 32 mg), Cs2CO3 (0.8 mmol, 261 mg), and anhydrous DMF (2.0mL). The tube was purged with argon, and the contents were stirred at 100 °C for 2 h.Then Na2S*9H2O (1.2 mmol, 240 mg) was added for 2 h. After reaction completion,the mixture was filtered through a pad of Celite, and DMF was removed by a vacuum.The combined filtrates were refluxed in THF (15 mL) and oxalic acid (1 M, 3 mL) for 8h. The solvents were removed under reduced pressure, then poured into brine (20mL) and extracted by ethyl acetate (3 × 30 mL). The combined organic layers weredried (Na2SO4) and evaporated. The residue was purified on a silica gel column usingpetroleum ether/ethyl acetate as the eluent to give the pure target product.

The synthetic route of 38573-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Fang-Ling; Chen, Zhen-Bang; Liu, Kui; Yuan, Qing; Jiang, Qing; Zhu, Yong-Ming; Synlett; vol. 29; 5; (2018); p. 621 – 626;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-fluoroaniline, 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 656-64-4, Application In Synthesis of 3-Bromo-4-fluoroaniline

Compound 3 (5 g, 30.9 mmol) was dissolved in 50 mL water and heated to 65 C.Further, Compound 4 (6.5 g, 34.0 mmol) was added, and then a saturated sodium hydrogen carbonate solution (50 mL) was added dropwise.After reacting for 1 hour, it was extracted with ethyl acetate, dried over anhydrous sodiumThe petroleum ether was passed through a column of ethyl acetate (4:1) to afford compound 5 (9 g, 92%) as white solid.

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-Bromo-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Xiangjin Biological Technology Co., Ltd.; Sun Fang; Zhan Youni; (38 pag.)CN109574950; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-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 51437-00-4, Computed Properties of C7H6BrF

Step 1. 5-Bromo-2-fluoro-3-methylbenzaldehyde: To a stirred solution of di- isopropyl amine (4.01 g, 39.88 mmol) in THF (20 mL) was added n-butyl lithium (1.6 M in hexane) (19.9 mL, 31.91 mmol) at -78 C slowly dropwise over the period of 10 min, the reaction mixture was stirred at -78C for 30 min. A solution of 4-bromo-l-fluoro-2- methylbenzene (5.0 g, 26.6 mmol) in THF (30.0 mL) was added at -78C, and the reaction mixture was stirred for lh at the same temperature. DMF (5.0 mL) was added and stirred at – 78C for another 30 min. The reaction was monitored by TLC; then the reaction mixture was quenched with IN HC1 solution (aq) at 0C. The aqueous layer was extracted with diethyl ether, washed with water and saturated brine solution. The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude compound purified by flash column chromatography (Si02, 100-200 mesh; eluting with 5% ethyl acetate/ pet ether) to afford the title compound as a white solid (3.6 g, 64 ); mp 48- 50C: ]H NMR (400 MHz, CDC13) delta 8.33 (s, 1H), 8.22 (s, 1H), 7.67 (s, 1H), 7.60 (s, 1H), 6.75 (dd, J = 17.6, 10.8 Hz, 1H), 5.92 (dd, J = 17.6, 10.8 Hz, 1H), 5.52 (d, J = 17.6 Hz, 1H), 2.21 (s, 3H); ESIMS m/z 211.35 ([M-H]”).

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

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); 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. 4101-68-2, name is 1,10-Dibromodecan, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,10-Dibromodecan

Tempol (0.01 mol) was added to a three-neck flask containing 100 ml dry benzene that is maintained at nitrogen atmosphere. To the flask, sodium hydride (0.015 mol) was added and kept refluxed for 24 hrs. The flask was cooled in ice bath and added 1,10-dibromodecane (0.02 mol) in one portion. The refluxing was then resumed for another 72 hrs. The contents of the flask was cooled in ice bath and added 25 ml water and transferred to a separatory funnel. The red upper benzene layer was separated , dried over anhydrous magnesium sulfate and solvent removed by rotory evaporation to get a red oil. The oil was purified by column chromatography on silica gel 60. The material was added to the column and eluted first with about 150 ml hexane that removed the excess of dibromodecane. The desired bromodecanoyl ether of Tempol was eluted with a mixture of hexane and ether (90:10). The red eluate was collected and was found to be pure on thin layer chromatography plates developed using the same solvent mixture. The yield was 0.008 mol (80%).

The synthetic route of 4101-68-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLBY PHARMACEUTICAL COMPANY; MEDICAL COLLEGE OF WISCONSIN, INC.; US2011/59922; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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. Application In Synthesis of 2-(4-Bromophenyl)ethanamine

[000449] Synthesis of tert-butyl (4-bromophenethyl) carbamate (547): To a stirred solution of 2-(4-bromophenyl) ethan-1-amine 546 (500 mg, 2.50 mmol) in CH2C12 (5 mL) under argon atmosphere were added Boc-anhydride (594 mg, 2.75 mmol), diisopropyl ethyl amine (1 mL, 7.50 mmol) at RT and stirred for 4 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (25 mL) and extracted with CH2C12 (235 mL). The combined organic extracts were washed with water (25 mL), dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 5-8% EtOAc/ hexanes to afford compound 547 (500 mg, 65%) as white solid. TLC: 10% EtOAc/ hexanes (R 0.5); 1H-NMR (DMSO-d6, 400 MHz): oe 7.46 (d, J= 8.0 Hz, 2H), 7.12 (d, J= 8.0 Hz, 2H), 6.86-6.82 (m, 1H), 3.12-3.08 (m, 2H), 2.68-2.64 (m, 2H), 1.32 (s, 9H).

The synthetic route of 73918-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary