Month: August 2021

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. 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(4-Bromophenyl)-N,N-dimethylmethanamine

To a 1 L round bottom flask with a stir bar, reflux condenser and gas inlet containing [4-bromophenyl)methyl]dimethyl amine (55 mmol, 11.8 g) in glyme (300 mL) and water (30 mL) was added 3-aminophenyl boronic acid hydrate (110 mmol, 17g), (Ph3P)2PdCI2 (2.75 mmol, 1.93 g) and sodium carbonate (165 mmol, 17.5 g). The reaction was stirred at reflux under nitrogen until LC-MS analysis indicated consumption of starting material. The reaction mixture was partitioned between diethyl ether and water. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated to give an oil. The oil was slurried in Et2O and acidified with 1N HCI in Et2O to give the HCI salt of the product as a precipitate (12 g, 73%). 1H NMR (300 MHz, DMSO-d6) delta ppm 8.15 (br s, 2H), 7.58 (d, 1 H, J = 7.3), 7.52 (d, 1H, J = 1.8), 7.34 (t, 1 H, J = 7.7), 7.22 (m, 2H)1 7.06 (m, 2H), 6.79 (d, 1H, J = 7.8), 4.32 (s, 2H), 2.73 (s, 6H)

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; SMITHKLINE BEECHAM CORPORATION; WO2007/18941; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 10485-09-3, name is 2-Bromoindene, 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. HPLC of Formula: C9H7Br

3.7 ml (30 mmol) of 2-Bromo-1H-indene was added to a flask, and Ar bubbling was performed for about 5 minutes while stirring in the presence of 100 ml of THF to remove dissolved gas. Under Ar bubbling, 0.8 g (1.5 mmol) of Ni(dppe)Cl2 was rapidly added and 30 ml (30 mmol) of 1.0 M ((Trimethylsilyl)methyl)magnesium chloride dissolved in diethyl ether at room temperature was slowly added dropwise. And then, the reaction was continued overnight while refluxing under Ar condition at 80 C. (dppe=1,2-Bis(diphenylphosphino)ethane) 50 mL of water was added thereto, and the organic layer was extracted three times with 50 mL of diethylether. An appropriate amount of MgSO4 was added to the collected organic layer, stirred for a while, filtered, and the solvent was dried under reduced pressure. The resulting product was confirmed by 1H-NMR (500 MHz, CDCl3): 0.03 (9H, s), 3.25 (2H, s), 6.3 (1H, s), 7.02-7.32 (4H, m)

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

Reference:
Patent; LG CHEM, LTD.; CHO, Kyung Jin; LEE, Ki Soo; LEE, Sung Min; HONG, Bog Ki; CHO, Min Seok; KIM, Se Young; HAN, Chang Woan; (27 pag.)US2018/79841; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 766-46-1, name is 2′-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 766-46-1

General procedure: A solution of1-iodo-2-methoxybenzene derivatives 5a-c or 1-iodo-2-methoxynathpthlene (5d) (1.0equiv.), 1-bromo-2-ethynylbenzene (6) (1.2 equiv.), Pd(PPh3)4 (5 mol%), and CuI (5 mol%) indegassed triethylamine and degassed THF was stirred at room temperature for 15 h under a nitrogenatmosphere. The reaction mixture was diluted with CHCl3 and washed with saturated NH4Cl aq. andbrine. The organic layer was dried over MgSO4. After removal of the solvent under reduced pressure,the residue was purified by chromatography on SiO2 to give the corresponding asymmetricdiarylacetylene derivatives 3a-d. The product 3a was characterized by comparing its spectral data withprevious report.[S1] The structures of the products 3b-d were assigned by their 1H and 13C-NMR, IR,mass spectra.

According to the analysis of related databases, 766-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Umeda, Rui; Shimizu, Yuji; Ida, Yuta; Ikeshita, Masahiro; Suzuki, Shuichi; Naota, Takeshi; Nishiyama, Yutaka; Tetrahedron Letters; vol. 60; 2; (2019); p. 183 – 186;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 176317-02-5, 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. 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 5-bromo-2,3,4-trifluorobenzoic acid To a solution of diisopropylamine (10.14 g, 100.20 mmol) in THF (100 mL) was added n-BuLi (40.08 mL, 2.5 M in hexane, 100.20 mmol) at -78 C. under nitrogen atmosphere. The stirring was maintained at this temperature for 1 h. Then a solution of 1-bromo-2,3,4-trifluorobenzene (17.62 g, 83.50 mmol) in THF (120 mL) was added. After stirring for 1 h at -78 C., the mixture was transferred to a bottle with dry ice. The mixture was stirred overnight at room temperature. The reaction was quenched with 10% aqueous HCl and pH was adjusted to 1-2. The mixture was extracted with ethyl acetate (100 mL*3). The combined organic extracts were washed with water (100 mL) and brine (100 mL) sequentially, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (20.12 g, 94.5% yield). 1H NMR (400 MHz, DMSO-d6): delta 13.95 (s, 1H), 7.97 (m, 1H).

The synthetic route of 1-Bromo-2,3,4-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIANJIN BINJIANG PHARMA, INC.; Tian, Hongqi; Ji, Conghui; Liu, Chunlei; Kong, Li; Cheng, Ying; Huang, Gongchao; US2014/371278; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 3344-70-5, name is 1,12-Dibromododecane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C12H24Br2

Example 11 (n=12); (a) 1,1′-[(Dodecane-1,12-diyl)dioxy]bis[(11S,11aS)-10-(tert- butyloxycarbonyl)-8-methoxy-11- (tetrahydro-pyran-2-yloxy)- 1, 2, 3, 10, 11, 11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazpeine-5- one] (8j); 1,12-Dibromododecane (73.1 mg, 0.22 mmol, 0.5 equiv) was added to the mixture of monomer 7 (0. 2 g, 0.44 mmol, 1.0 equiv) potassium carbonate (0.98 mmol, 2. 2 equiv) and a catalytic amount of potassium iodide in dry DMF (30 mL), and the resulting mixture was heated to 90°C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (SiO2, 50percent EtOAc- hexane) to afford the dimerized compound 8j (208 mg, 0.19 mmol, 87percent yield, mixture of diastereomers from THP protecting group) as a solid: [alpha]20D = +50° (c = 0.20, CHC13) ; 1H NMR (CDCl3, 400 MHz): No. 1.26-1. 68 (m, 84H, 14-H, 15-H, 16-H, 17-H, Boc, THP), 1.69-1. 89 (16H, 13-H, THP), 1.93-2. 20 (m, 16H, 1-H, 2-H), 3.44-3. 75 (m, 16H, 3-H, lla-H, THP), 3.83-4. 14 (m, 24H, 12-H, 7-OMe, THP), 5.02-5. 10 (m, 2H, THP), 5.12-5. 19 (m, 2H, THP), 5.69-5. 77 (d, 2H, 11-H), 5.79-5. 89 (d, 2H, 11-H), 6.50 (s, 2H, 9-H), 6.87 (s, 2H, 9-H), 7.19 (s, 2H, 6-H), 7.22 (s, 2H, 6-H) ;”C NMR (CDCl3, 400 MHz): 5 19.9, 20.4, 23.1, 23.2, 25.2, 25.3, 25.9, 28.1, 28.2, 28.9, 29.0, 29.1, 29.2, 29.3, 29.56, 29.58, 30.9, 31.2, 46.2, 55.9, 56.2, 60.0, 60.1, 63.3, 64.4, 69.12, 69.15, 80. 9,81. 2,88. 2,91. 2, 95.8, 100.2, 111.1, 111.5, 113.4, 114.0, 126.3, 129.6, 134. 1, 138.8, 147.8, 148.1, 151.5, 155.3, 167.4, 167.6 ; IR (neat): 2932, 1703,1643, 1604,1513, 1450,1392, 1327,1218, 1164, 1022cm~1 ; MS (FAB) m/z (relative intensity) 1085 ( + Na] +, 28), 1063 (M 100), 961 (17), 861 (13).

According to the analysis of related databases, 3344-70-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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. SDS of cas: 337915-79-4

Example 62 4- ( ( 4-Chlorobenzyl) oxy) -1- (2- (2, 2-difluorocyclopropyl) -1- methyl-lH-benzimidazol-6-yl ) pyridin-2 (1H) -one A) 6-Bromo-2- (2, 2-difluorocyclopropyl) -1-methyl-lH- benzimidazole A. mixture of 5-bromo-N1-methylbenzene-l, 2-diamine (300 mg) , HATU (567 mg) , N, N-diisopropylethylamine (0.255 ml), 2,2- difluorocyclopropanecarboxylic acid (182 mg) and DMF (10 ml) was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04, passed through NH silica gel pad and concentrated in vacuo. The precipitate was washed with IPE/hexane, collected by filtration and dried in vacuo to give the title compound (255 mg) as a yellow solid. MS (ESI+) : [M+H]+ 288.9.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 626-88-0, A common heterocyclic compound, 626-88-0, name is 1-Bromo-4-methylpentane, molecular formula is C6H13Br, 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.

Into a 15-mL sealed tube, was placed a solution of 1-bromo-4-methylpentane (5 g, 30.30 mmol, 2.00 equiv) in 1,3-dimethylimidazolidin-2-one (20 mL), methyl 4-iodobenzoate (4 g, 15.27 mmol, 1.00 equiv), NiI2.6H2O (0.68 g, 1.62 mmol, 0.11 equiv), Mn (1.66 g, 30.18 mmol, 2.00 equiv), pyridine (0.12 g, 1.52 mmol, 0.10 equiv), 4,4′-di-tert-butyl-2,2′-bipyridine (0.204 g, 0.76 mmol, 0.05 equiv) and 1,2-bis(diphenylphosphino)benzene (0.338 g, 0.76 mmol, 0.05 equiv). The reaction mixture was stirred overnight at 85 C. in an oil bath and then quenched by the addition of 100 mL of water, then cooled to room temperature. The resulting mixture was extracted with 3*100 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether (100%) to yield of methyl 4-(4-methylpentyl)benzoate as colorless oil.

The synthetic route of 626-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Gaul, Micheal; Xu, Guozhang; Zhao, Bao-Ping; (53 pag.)US2018/64686; (2018); A1;,
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. 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H6BrF

PROCESS EXAMPLE 13 2-(p-Fluoro-m-methylphenyl)-6-isopropylphenol (scheme 1, formula IX) In analogy to Process Example 2, the title compound was obtained from 2-bromo-6-isopropylphenol (from Process Example 1) and the Grignard reagent from p-fluoro-m-methylbromobenzene in 68% yield as a colorless solid. NMR (60 MHz): delta=1.25 (d, 6H, CH3), 2.35 (s, 3H, CH3), 3.30 (sept., 1H, CH), 5.00 (s, br, 1H, OH), 6.7-7.5 (m, 6H, arom. MS (DCI, isobutane): m/e=245 (M+H+), 244 (M+), 229 (M+ –CH3).

The synthetic route of 51437-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US5294724; (1994); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 52723-82-7, name is 4-Bromo-5-fluoro-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 52723-82-7

EXAMPLE 47 4-Amino-2-fluoro-5-methylbenzonitrile Using the method of Example 15, 4-bromo-3-fluoro-6-methylaniline is converted into the title compound.

According to the analysis of related databases, 52723-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US4863959; (1989); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, 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 68322-84-9, Quality Control of 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene

EXAMPLE 60 (2S)-1-[((2S,5R)-5-{[2-bromo-4-(trifluoromethyl)phenoxy]methyl}pyrrolidin-2-yl)carbonyl]pyrrolidine-2-carbonitrile The compound of Example 14A (50 mg, 0.15 mmol) and 3-bromo-4-fluorobenzotrifluoride (30 muL, 0.2 mmol) were stirred in DMF (1 mL) under N2. NaH (13 mg, 0.3 mmol) was added to the mixture. It was stirred at room temperature for I hour. After the reaction was over, the mixture was purified by reverse-phase HPLC to give the Boc-protected compound (40% yield). MS (ESI) m/z 546, 548 (M+H)+. The Boc group was removed according to Example 1G to give the title compound. 1H NMR (500 MHz, MeOH-d4) delta ppm 2.05-2.44 (m, 7 H), 2.49-2.65 (m, 1 H), 3.50-3.59 (m, 1 H), 3.62-3.74 (m, 1 H), 4.20-4.32 (m, 1 H), 4.47-4.58 (m, 2 H), 4.68-4.76 (m, 1 H), 4.81-4.90 (m, 1 H), 7.27 (dd, J=8.42, 4.05 Hz, 1 H), 7.69 (d, J=8.73 Hz, 1 H), 7.85-7.94 (m, 1 H). MS (ESI) m/z 446, 448 (M+H)+.

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; Pei, Zhonghua; Li, Xiaofeng; Longenecker, Kenton L.; Sham, Hing L.; Wiedeman, Paul E.; US2005/131019; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary