Category: bromides-buliding-blocks

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. 3814-30-0 name is (Bromomethyl)cyclopentane, 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. 3814-30-0

EXAMPLE 51A Methyl 3-cyclopentyl-2-methyl-2-phenylpropanoate A solution of lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 3.04 mL, 3.04 mmol, 1 equiv) under a N2 atmosphere was cooled to 0 C. and treated with a solution of methyl 2-phenylpropionate (0.500 g, 3.04 mmol, 1 equiv) in dry tetrahydrofuran (2 mL). The reaction was stirred at 0 C. for 2 hrs, then cooled to -78 C. and treated with hexamethylphosphoric triamide (0.4 mL) and bromomethylcyclopentane (0.745 g, 4.568 mmol, 1.5 equiv). Stirred the reaction at -78 C. and allowed the bath to slowly warm to room temperature overnight. After 15 hrs, the reaction mixture was quenched with 10% aq NH4Cl (50 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with H2O (50 mL) and brine, then dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was purified by SiO2 flash chromatography with 2:3 dichloromethane/hexanes to give the product as colorless oil (1.38 g, 5.60 mmol, 92%). 1H NMR (300 MHz, DMSO-d6): delta ppm 0.90-1.12 (m, 2H) 1.32-1.72 (m, 10H) 1.97-2.12 (m, 2H) 3.58 (s, 3H) 7.19-7.35 (m, 5H); MS (APCI+) m/z 247 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Bromomethyl)cyclopentane, and friends who are interested can also refer to it.

Reference:
Patent; Hutchinson, Douglas K.; Bellettini, John R.; Betebenner, David A.; Bishop, Richard D.; Borchardt, Thomas B.; Bosse, Todd D.; Cink, Russell D.; Flentge, Charles A.; Gates, Bradley D.; Green, Brian E.; Hinman, Mira M.; Huang, Peggy P.; Klein, Larry L.; Krueger, Allan C.; Larson, Daniel P.; Leanna, M. Robert; Liu, Dachun; Madigan, Darold L.; McDaniel, Keith F.; Randolph, John T.; Rockway, Todd W.; Rosenberg, Teresa A.; Stewart, Kent D.; Stoll, Vincent S.; Wagner, Rolf; Yeung, Ming C.; US2005/107364; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, I believe this compound will play a more active role in future production and life. 28342-75-8

l,5-Dibromo-2,4-difluorobenzene (1, 1.36 g, 5.00 mmol) was dissolved in dry diethyl ether ( 15 mL) and cooled down to -78C. 2.35 M n-Butyllithium in hexane (2.20 mL, 5.25 mmol) was added drop-wise with stirring . After 15 minutes, dry N,N- dimethylformamide (0.77 mL, 10.0 mmol) was added and the resulting mixture was stirred at for 15 minutes and then allowed to warm to ambient temperature. After one hour, the reaction mixture was quenched with 1.0 M aqueous solution of hydrochloric acid ( 15 mL) . Layers were separated and the organic layer was washed with brine ( 15 mL), dried over anhydrous magnesium sulfate and evaporated . The residue was purified by flash column chromatography (Silicagel 60, 0.063-0.200 mm ; eluent: cyclohexane/ ethyl acetate 20 : 1) 5-bromo-2,4-difluorobenzaldehyde (2) as colorless oil which solidified on storage in freezer. Yield : 780 mg (70%) . JH NM R spectrum (300 MHz, CDCI3, deltaEta) : 10.26 (s, 1 H) ; 8.14 (dd, J =9.6 and 8.0 Hz, 1 H) ; 7.05 (d, J = 8.0 Hz, 1 H) .

The chemical industry reduces the impact on the environment during synthesis 28342-75-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVO NORDISK A/S; KRUSE, Thomas; HANSEN, Mikael, Kofoed; MUeNZEL, Martin, Werner, Borchsenius; TH?GERSEN, Henning; SAUERBERG, Per; RASMUSSEN, Jakob, Ewald; BEHRENS, Carsten; H?EG-JENSEN, Thomas; BAL?ANEK, Vojtech; DROBNAKOVA, Zuzana; DRO?, Ladislav; HAVRANEK, Miroslav; KOTEK, Vladislav; ?TENGL, Milan; ?NAJDR, Ivan; VANOVA, Hana; (202 pag.)WO2019/92125; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 1646-54-4, name is 1,4-Dibromo-2,3,5,6-tetramethylbenzene, molecular formula is C10H12Br2, 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. 1646-54-4.

The reaction pathway is shown in Scheme 1. H4dbtec ligand was prepared according literature [13] and with a little modification. To a four-necked flask equipped with a reflux condenser and a mechanical stirrer, 3,6-bromo-tetramethylbenzene (0.171 mol), 2.1 L pyridine and 280 mL water were added. The reaction mixture was heated to 100 C while stirring. KMnO4 (0.859 mol) was added in small portions and the mixture was refluxed for 5 h. The warm solution was separated from MnO2 by filtration and the solvent evaporated under reduced pressure. 280 mL water and 112 g NaOH were added to the residual solid. After the combined mixture was heated up to 100 C, KMnO4 (0.859 mol) was added again in small portions and the mixture was refluxed for 5 h. The excess KMnO4 was destroyed by the cautious addition of 140 mL ethanol. The MnO2 was removed from the hot mixture by filtration. The filtrate was acidified with aqueous HCl (5 M, 600 mL). After the solvent was revaporated, the residue was washed with acetone. The resultant solid was dried. The yield was 46 g (66%). 1H NMR (300 MHz; DMSO-d6) no signals. 13C NMR (100 MHz; DMSO-d6) deltac 115.51, 137.57, 166.27.

The synthetic route of 1,4-Dibromo-2,3,5,6-tetramethylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Liang-Liang; Guo, Yu; Wei, Yan-Hui; Guo, Jie; Wang, Xing-Po; Sun, Dao-Feng; Journal of Molecular Structure; vol. 1038; (2013); p. 73 – 77;,
Bromide – Wikipedia,
bromide – Wiktionary

39478-78-9, Adding some certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9.

General procedure: In a typical run, h-BN(at)Fur(at)Pd(OAc)2 (0.05 mmol) was added to a mixture of arylboronic acid 1 (1.0 mmol), aryl bromide 2 (1.5 mmol) and K2CO3 (1.5 mmol) in water (1 mL). The resulting mixture was stirred at 70 C under Ar protection, and the progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added to the reaction mixture and the catalyst was separated. The organic phase was washed with water, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. Finally, the residue was isolated by chromatography on a column of silica gel to afford the corresponding product 3.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 39478-78-9.

Reference:
Article; Li, Weijian; Lv, Guanghui; Cheng, Xu; Sang, Rui; Ma, Xiaojun; Zhang, Yong; Nie, Ruifang; Li, Jie; Guan, Mei; Wu, Yong; Tetrahedron; vol. 72; 52; (2016); p. 8557 – 8564;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 4549-32-0, name is 1,8-Dibromooctane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 4549-32-0

General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product.

The synthetic route of 4549-32-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Saied, Essa M.; Le, Thuy Linh-Stella; Hornemann; Arenz, Christoph; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4047 – 4057;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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. 3814-30-0

EXAMPLE 136 4-(4-Chloro-3-cyclopentylmethylsulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ole 6.7 g of 4-(4-Chloro-3-sulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ole (Example 2) were introduced, while stirring, into a mixture of 10 ml of absolute dimethyl sulfoxide and 1.2 g of pulverized potassium hydroxide with the exclusion of nitrogen, the temperature being maintained between 8 C and 12 C by outward cooling. While cooling and stirring were maintained, 3.3 g of cyclopentylmethylbromide were added dropwise, the mixture was stirred for 10 hours at room temperature and precipitated with 100 ml of water. The oily residue was decanted, the amorphous product was solidified under 100 ml of fresh water, suction-filtered and washed with water several times. Yellow-brown solid substance, decomposition beginning at 72 C. The IR-spectrum was identical with that of Example 76.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3814-30-0.

Reference:
Patent; Hoechst Aktiengesellschaft; US4061761; (1977); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 2695-47-8, name is 6-Bromo-1-hexene, molecular formula is C6H11Br, 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. 2695-47-8

Step A: Preparation of 2,2,2-trifluoro-N-(hex-5-enyl)-N-methylacetamide 1a. At 0 C. and under nitrogen atmosphere, sodium hydride (60% dispersion in mineral oil, 31.5 g, 1.28 eq.) was slowly added to a cooled solution of N-methyl-2,2,2-trifluoroacetamide (100 g, 1.28 eq.) in DMF (500 mL). The reaction mixture was stirred for 2 hrs at 0 C. and 6-bromo-1-hexene (100 g, 1 eq.) was added dropwise for 45 min. The reaction mixture was allowed to warm up to room temperature and was stirred for 3 days. The reaction mixture was poured into water and extracted three times with EtOAc. The combined organic layers were dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The resulting residue was purified by chromatography on silica gel (petroleum ether/EtOAc) to yield compound 1a as colourless oil in 56% yield. 1H NMR (DMSO-d6, 400 MHz) delta (ppm) 1.27-1.38 (m, 2H), 1.48-1.60 (m, 2H), 2-2.06 (m, 2H), 2.93 (m, 3H), 3.35-3.40 (m, 2H), 4.92-5.04 (m, 2H), 5.73-5.83 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2695-47-8, its application will become more common.

Reference:
Patent; Idenix Pharmaceuticals, Inc.; US2010/260710; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, The chemical industry reduces the impact on the environment during synthesis 55289-36-6, name is 3-Bromo-2-methylaniline, I believe this compound will play a more active role in future production and life.

31 mL of 1N sulfuric acid aqueous solution was added to 3-bromo-2-methylaniline (4.04 g, 21.7 mmol), andthe mixture was cooled to 0C. Sodium nitrite (6.0 M aqueous solution, 4.3 mL) was slowly added thereto. After 15minutes, 10 mL of sulfuric acid was added thereto, and the mixture was stirred for 1 hour under reflux. The reactionsolution was cooled to room temperature. After addition of water, the reaction solution was extracted with Et2O. Theorganic layer was dried with anhydrous magnesium sulfate and purified by column chromatography to obtain the titlecompound (2.34 g, 58 %).1H-NMR (CDCl3) delta 7.14 (1H, d), 6.92 (1H, t), 6.71 (1H, d), 4.83 (1H, brs), 2.34 (3H, s)

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

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, A common compound: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

1.6 M n-BuLi in hexane (7.94 mL, 12.70 mmol) was added to a solution of bis ( isopropyl ) amine (2.246 mL, 15.87 mmol) in THF(dry) (10 mL) at -78 C. The mixture was stirred at -7.8 C under Ar for 30 min. The solution of 4-bromo-l-fluoro-2- methylbenzene (1.338 mL, 10.58 mmol) in THF was added. The mixture was stirred at -78 C under Ar for 1 h. Propan-2-one (0.935 mL, 12.70 mmol) was added. The mixture was stirred at – 78C under Ar for 2 h. The mixture was poured into IN HC1 aq. and extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 3% – 12% EtOAc in hexane) to give the title (4065) compound (1.780 g, 7.20 mmol, 68.1%) as white solids. (4066) 1H NMR (300 MHz, DMSO-d6) 5:1.-46 (6H, d, J = 1.1 Hz), 2.21 (3H, d, J = 2.6 Hz), 5.39 (1H, s), 7.32-7.42 (1H, m) , 7.55 (1H, dd, J = 6.8, 2.6 Hz) .

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; SHIOKAWA, Zenyu; YUKAWA, Tomoya; IMADA, Takashi; NEGORO, Nobuyuki; ODA, Tsuneo; SASAKI, Satoshi; NARA, Yoshi; SUZUKI, Shinkichi; SATO, Ayumu; ISHII, Naoki; SHIBUYA, Akito; NAKAGAWA, Yasuo; COLE, Derek; GIBSON, Tony; IVETAC, Anthony; SWANN, Steve; TYHONAS, John; (472 pag.)WO2018/30550; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 344-03-6, name is 1,4-Dibromotetrafluorobenzene, molecular formula is C6Br2F4, 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. 344-03-6.

A mixture of 5,5′-bis(tri-n-butylstannyl)-2,2′-dithiophene (4.62 g, 4.87 mmol), 1,4-dibromoperfluorobenzene (6.00 g, 19.48 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.10 mmol) in dry DMF (20 mL) was deareated twice with nitrogen. The reaction mixture was then heated at 85¡ã C. for 20 h during which time a precipitate formed. After cooling, the orange solid was collected and washed several times with hexane and ether to afford the crude product which was purified by gradient sublimation (2.14 g, 3.42 mmol, 70.2percent yield). M.p. 231¡ã C. 1H NMR (CDCl3) delta 7.60 (2H, d, 2J=4.1), 7.34 (2H, d); 19F NMR (CDCl3) delta -133.58 (4F), -138.56 (4F). Anal. Calcd for C20H4Br2F8S2: C, 38.72; H, 0.65; F, 24.51. Found: C, 38.75; H, 0.78; F, 24.29.

The synthetic route of 1,4-Dibromotetrafluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Marks, Tobin J.; Facchetti, Antonio; US2008/293937; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary