Month: February 2021

Electric Literature of 4549-33-1,Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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: Compound 2a or 2b (2 mmol) and KOH (0.34 g, 6 mmol) weredissolved in acetonitrile. The solution was stirred for 1 h under argonat room temperature. Then, different dibromoalkanes(4 mmol) were added to the mixture. After stirring for 48 h, themixture was filtered and evaporated under reduced pressure. Theresidue was chromatographed on silica gel, with petroleumether/ethyl acetate, 10:1, plus 10 mL triethylamine per 1000 mLas the eluent to afford the compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,9-Dibromononane, its application will become more common.

Reference:
Article; Sun, Yang; Chen, Jianwen; Chen, Xuemin; Huang, Ling; Li, Xingshu; Bioorganic and Medicinal Chemistry; vol. 21; 23; (2013); p. 7406 – 7417;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2862-39-7, 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. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, This compound has unique chemical properties. The synthetic route is as follows.

A stirred mixture of 3,3-bis(4-hydroxyphenyl)-2-(thiophen-2-yl)acrylonitrile (11; 30 mg, 0.1 mmol), 2-bromo-N,N-dimethylethylamine hydrobromide (328 mg, 1.4 mmol), cesium carbonate (612 mg, 1.9 mmol), and acetonitrile (3 mL) was heated at reflux for 18 h. The mixture was diluted with water and extracted with ethyl acetate (3x). The combined extracts were washed successively with water and sat. brine, dried and concentrated to a syrup that was purified by flash silica gel chromatography, eluting first with 4-5 column volumes of 3:1 dichloromethane/methanol and then with 95:5 methanol/conc. ammonium hydroxide to elute the product. Combined product fractions were concentrated to leave 12 (18 mg, 42%) as an amber gum. HPLC: rt 5.1 min (89% purity). 1H NMR (400 MHz, DMSO-d6): delta 7.46 (d, J = 5.2 Hz, 1H), 7.32 (d, J = 8.9 Hz, 2H), 7.17 (d, J = 2.5 Hz, 1H), 7.08 (d, J = 8.8 Hz, 2H), 7.03-6.87 (m, 5H), 4.15-3.97 (m, 4H), 2.65-2.53 (m, 4H), 2.20 (s, 12H). MS TOFES+: m/z 462.1 (M+H)+.

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

Reference:
Article; Carpenter, Colleen; Sorenson, Roderick J.; Jin, Yafei; Klossowski, Szymon; Cierpicki, Tomasz; Gnegy, Margaret; Showalter, Hollis D.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5495 – 5504;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 126930-72-1,Some common heterocyclic compound, 126930-72-1, name is 1-Bromo-4-dodecylbenzene, molecular formula is C18H29Br, 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.

(0236) To a suspension of 1-bromo-4-dodecylbenzene (2.2 g, 6.8 mmol) in anhydrous tetrahydrofuran (50 cm3) at -78 C. was added dropwise tert-butyllithium (7.2 cm3, 14 mmol, 1.9 M in pentane) over 30 minutes. After addition, the reaction mixture was stirred at -78 C. for 1 hour. 5,5?-Bis-triisopropylsilanyl-[2,2?;5?,2?]ter[thieno[3,2-b]thiophene]-3?,6?-dicarboxylic acid diethyl ester 3 (1.0 g, 1.1 mmol) was then added in one portion. The reaction mixture was then stirred at -78 C. for 2 hours and at 23 C. for 17 hours. The reaction mixture was poured into water (150 cm3) and the organics extracted with diethyl ether (5¡Á50 cm3). The combined organics were washed with brine (100 cm3), dried over anhydrous magnesium sulphate, filtered and the solvent removed in vacuo. The crude was purified by column chromatography (n-pentane) to give {6?[bis-(4-dodecyl-phenyl)-hydroxy-methyl]-5,5?-bis-triisopropylsilanyl-[2,2?;5?,2?]ter[thieno[3,2-b]thiophene]-3?-yl}-bis-(4-dodecyl-phenyl)-methanol 4 (800 mg, 40%) as a colourless oil. (0237) 1H-NMR (300 MHz, CDCl3) 0.84-0.92 (12H, m), 1.06-1.17 (36H, m), 1.21-1.37 (78H, m), 1.54-1.66 (8H, m), 2.53-2.63 (8H, m), 3.45 (2H, s), 6.50 (2H, s), 7.08 (8H, d, J 8.3), 7.17 (2H, s), 7.20 (8H, d, J 8.3)

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-4-dodecylbenzene, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; MITCHELL, William; D’LAVARI, Mansoor; WANG, Changsheng; SPARROWE, David; (45 pag.)US2016/301008; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1422-54-4, name is 2-Bromo-6-fluorotoluene, 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 1422-54-4, HPLC of Formula: C7H6BrF

1-BROMO-3-FLUORO-2-METHYL-BENZENE (189 mg, 1.0 MMOL) was dissolved in 4 mL dry 1,4-dioxane under an argon atmosphere. Compound 402 (304 mg, 1.00 MMOL) was added and dissolved in the solvent. DICYCLOHEXYL-(2 , 4 , 6 -TRIISOPROPYL-BIPHENYL-2-YL)- phosphane (19 mg, 0.04 MMOL), Pd (OAc) 2 (5 mg, 0.02 MMOL) and CS2CO3 (407 mg, 1.25 MMOL) were added, and the reaction mixture was stirred under an argon atmosphere at 120 C for 60 h. The reaction mixture was filtered and then purified by flash chromatography using EtOAc/petroleum ether (40-60) 1: 4 as the eluent to afford the title compound as a SOLID. 13C NMR (CI3) S

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; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
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 698-00-0 as follows. name: 2-Bromo-N,N-dimethylaniline

General procedure: In a fume hood, an oven-dried Schlenk flask equipped with magnetic stirring bar was filled with N2 and evacuated (three cycles). Under N2 atmosphere, Pd(OAc)2 (1.1 mg, 0.005 mmol, 1 mol% Pd), SPhos (4.1mg, 0.01 mmol, 2 mol%), K3PO4 (160 mg, 1.5 mmol, 1.5 equiv), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-bis(trifluoromethyl)pyridine (1, 171 mg, 0.5 mmol, 1 equiv), aryl bromide (0.75 mmol,1.5 equiv), and DME (2 mL) were added in order. The Schlenk flask was closed and the mixture was heated at 80 C in an oil bath for 24-48 h. The progress of reaction was monitored by GC-MS and TLC. Upon completion of reaction, the Schlenk flask was cooled to r.t. and exposed to air. The mixture was extracted into EtOAc, washed with water and brine, and dried (anhyd Na2SO4). The crude product was purified by column chromatography (silica gel). For chloro-substituted bromoarenes (2g, 2h, and 2m), Pd(PPh3)4 (23mg, 0.02 mmol, 4 mol% Pd) was used (for 1-mmol scale reaction) in place of Pd(OAc)2 and SPhos. Unless otherwise noted, reactions were performed on a 0.5-mmol 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-bis(trifluoromethyl)pyridine (1) scale.

According to the analysis of related databases, 698-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Batool, Farhat; Emwas, Abdul-Hamid; Gao, Xin; Munawar, Munawar A.; Chotana, Ghayoor A.; Synthesis; vol. 49; 6; (2017); p. 1327 – 1334;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 583-68-6,Some common heterocyclic compound, 583-68-6, name is 2-Bromo-4-methylaniline, molecular formula is C7H8BrN, 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-isocyano-5-methyl-biphenyl (1a):To a dry three necked flask, 2-bromo-4-methylaniline(S1,3.7 g, 20 mmol), phenylboronic acid (2.9 g, 24 mmol), aqueous solution of K2CO3 (2M, 15 mL) and DME (15 mL) were added,and the mixture was stirred for 30 min at room temperature under Ar atmosphere.To the stirred mixture, PdCl2 (PPh3)2 (280mg, 0.40 mmol) was added at room temperature, and the mixture was stirred for overnight at 80 C, under Ar. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The organic layer was washed with water and dried over anhydrous MgSO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography on silica gel(petroleum ether/EtOAc = 30/1) to afford 4-methyl-2-phenylaniline as yellow oil (S2, 3.2 g, 87%). Acetic formic anhydride, which was prepared from the reaction of acetic anhydride (1.3 mL) with formic acid (0.6 mL) at 55 C for 2 h, was added dropwise to a stirred solution of S2 (1.10 g, 6 mmol) at 0 C in THF (10 mL) and the mixture was stirred for 2 h at room temperature. Then, the mixture was quenched by sat.aqueous solution of NaHCO3 and extracted with EtOAc three times. The extract was dried over Na2SO4 and concentrated under reduced pressure to give formamide S3 as pale yellow oil. This material was used for the subsequent dehydration without further purification. THF (10 mL), NEt3 (6 mL) and the whole amount of S3 obtained above were added and cooled to 0 C.Then, POCl3 (0.9 mL, 10 mmol) was added dropwise, and the mixture was stirred at 0 C for 2 h. After the reaction was completed, the mixture was quenched by sat. aqueous solution of Na2CO3 and stirred for 1 h. The mixture was extracted with CHCl3 three times, dried over MgSO4 and evaporated under reduced pressure. The compound was purified by column chromatography on Florisil (hexane/EtOAc = 20/1) to give 1a as a white solid (0.89 g, 77% yield from S2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methylaniline, its application will become more common.

Reference:
Article; Wang, Gao; Chen, Shan-Yong; Yu, Xiao-Qi; Tetrahedron Letters; vol. 55; 38; (2014); p. 5338 – 5341;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-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 1003-99-2, category: bromides-buliding-blocks

General procedure: In the MW method, a mixture of 4-chloro-5,6,7-trimethoxyquinazoline (3.0 mmol) and aryl amine (3.0 mmol) in 2-propanol (10 mL) was stirred for 3 min and then reacted under MW at 100 W and 80 ¡ãC for 20 min. Upon reaction completion as monitored by thin-layer chromatography (TLC), the solvent was removed under reduced pressure. The residue was dissolved with methanol or chloroform and purified by TLC (petroleum ether/ethylacetate, 1:2, V:V). The target compound was eluted from the silica gel with ethyl acetate to give the title compounds.

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:
Article; Zhang, Ying; Jin, Linhong; Xiang, Hongmei; Wu, Jian; Wang, Peiyi; Hu, Deyu; Xue, Wei; Yang, Song; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 335 – 344;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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. Application In Synthesis of (4-Bromo-2-fluorophenyl)methanamine

Step 1 : To a stirred solution of (4-bromo-2-fluorophenyl)methanamine (5.834 g, 28.592 mmol) in pyridine were added methanesulfonyl chloride (4.2 ml_, 54.325 mmol) at 0 C. The reaction mixture was stirred for 1 h, then diluted with dichloromethane. The mixture was washed with water. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. N-(4-bromo-2- fluorobenzyl)methanesulfonamide (7.597 g) was obtained as 93 % yield.

The synthetic route of (4-Bromo-2-fluorophenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/45452; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 50548-45-3, A common heterocyclic compound, 50548-45-3, name is 1-Bromodibenzo[b,d]furan, molecular formula is C12H7BrO, 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.

To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),1,1′-biphenyl] -4-yl) – [1,1 ‘: 3′, 1 ” – terphenyl(N – ([1,1’-biphenyl] -4-yl) – [1,1 ‘: 3’, 1 ” – terphenyl]”(17.75 g, 44.72 mmol) Xylene(Xylene) in 260 mlAfter completely dissolvedSodium tert-butoxide(sodium tertbutoxide) (5.08 g, 52.85 mol) was added,Bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0)) (0.21 g, 0.41 mmol)And the mixture was heated and stirred for 7 hours.The temperature was lowered to room temperature and filteredAfter the salt was removed, xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to obtain Compound (3) (16.17 g, yield: 71percent).

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; LG CHEM, LTD.; KIM, Jin Joo; HONG, Sung gil; CHA, Yong bum; (27 pag.)KR2017/94665; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2550-36-9, 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. 2550-36-9, name is (Bromomethyl)cyclohexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The first step of Scheme 19: To a solution of 4-bromo-3-ethoxycarbonylmethoxy-5-(3-hydroxy-phenyl)-thiophene-2-carboxylic acid methyl ester in DMF was added bromomethyl-cyclohexane (21 muL) and K2CO3 (27.6 mg). The resultant suspension was stirred at room temperature, then heated to 80 C. until the disappearance of the starting material as monitored by TLC. The reaction mixture was cooled to room temperature and diluted with EtOAc, and filtered through a pad of Celite, rinsed with EtOAc. The solvent was removed, the crude product was purified on CombiFlash column eluting with hexane/EtOAc to give the desire product, 4-bromo-3-ethoxycarboxymethoxyl-5-3-cyclohexylmethoxy-phenyl)-thiophene-2-carboxylic acid methyl ester (44 mg, 85%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 1.2 (m, 8H) 1.8 (m, 6H) 3.8 (d, J=6.3 Hz, 2H) 3.9 (s, 3H) 4.3 (q, J=7.1 Hz, 2H) 4.9 (s, 2H) 7.0 (m, 1H) 7.2 (m, 2H) 7.3 (m, 1H).

The synthetic route of (Bromomethyl)cyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Jinbo; Wan, Zhao-Kui; Wilson, Douglas P.; Follows, Bruce C.; Kirincich, Steven J.; Smith, Michael J.; Wu, Jun-Jun; Foreman, Kenneth W.; Erbe, David V.; Zhang, Yan-Ling; Xu, Weixin; Tam, Steve Y.; US2005/203087; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary