Tag: M.W=100-200

Some common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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. Application In Synthesis of 1-Bromo-2-cyclohexylethane

REFERENCE EXAMPLE 13 2-Cyclohexyl-N-(2-hydroxyethyl)ethylamine Hydrochloride (Reference Compound No. 13-1) Anhydrous potassium carbonate (3.5 g) and sodium iodide (9.4 g) are added to a solution of 2-aminoethanol (1.9 ml) and 2-cyclohexylethyl bromide (4.0 g) in ethanol (42 ml), and the mixture is refluxed for 17 hours with stirring. A saturated aqueous ammonium chloride solution is added to the reaction mixture, and the mixture is washed with ether. A 4 N aqueous sodium hydroxide solution is added to the aqueous layer, and the whole is extracted with chloroform. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is dissolved in ethyl acetate. To the solution are added a 4 N solution of hydrogen chloride in ethyl acetate (4 ml) and then ether (10 ml) under ice cooling, and the resulting precipitate is filtered off to give 2.2 g (51%) of the titled compound (Reference compound No. 13-1) as crystals. (Reference Compound No. 13-1) mp 158.5~160.2 C.; IR (KBr, cm-1) 3316, 2922, 2856, 1560, 1467, 1454, 1407, 1351, 1084, 1058, 1049, 1001, 932.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1647-26-3, its application will become more common.

Reference:
Patent; Santen Pharmaceutical Co., Ltd.; US6492370; (2002); B1;,
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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. 103-64-0, name is (2-Bromovinyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of (2-Bromovinyl)benzene

To a solution of N, N-dimethylformamide (DMF) in a volume ratio of 4: 1 with polyethylene glycol 200(PEG-200)) was added 100 mmol of the compound of the above formula (I), 40 mmol of the compound of the above formula (II), 11 mmol of catalyst bis (triphenylphosphine) cyclopentadienyl ruthenium chloride,100 mmol of oxidant bis (trifluoroacetic acid) iodobenzene (PhI (TFA) 2), 20 mmol of organic ligand L1 and 60 mmol of base, 5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) Then the mixture was warmed to 70 C with stirring, and the reaction was stirred at that temperature for 12 hours;After completion of the reaction, the reaction system is naturally cooled to room temperature and the pH is adjusted to neutral, filtered and the filtrate is saturatedSalt water washing, and then extracted with ethyl acetate 2-3 times,The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography,Was eluted with a mixture of chloroform and petroleum ether in a volume ratio of 1: 2 to give the compound of the above formula (III) in a yield of 77.3%.

The synthetic route of 103-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Cheng; No proclaimed inventor; (12 pag.)CN106278839; (2017); A;,
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Reference of 2695-48-9, 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. 2695-48-9 name is 8-Bromo-1-octene, 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.

General procedure: Part of the solution of 8-bromo-1-octene (573.3 mg, 3.0 mmol) in THF (2 mL) was quickly addedvia syringe to a stirred solution of Mg (1.16 g, 5.0 mmol) and I2 (cat.) in THF (5 mL) under Aratmosphere. The mixture was heated until the color disappeared; then, the remaining 8-bromo-1-octene was added dropwise. After the addition was completed, the resulting reaction mixture washeated to reflux for 1 h and then was allowed to cool to room temperature. The prepared Grignardreagent was added slowly to a solution of D-arabino-nitrone (14) (417.5 mg, 1.0 mmol) in THF (10 mL)via syringe at 0 C under Ar atmosphere. The reaction mixture was stirred for 0.5 h; then sat. aq.NH4Cl was added to quench the reaction. The organic layer was separated and the aqueous layer wasextracted with EtOAc (3 ¡Á 20 mL). The combined organic phases were dried over MgSO4 and filtered;the solvent was removed under reduced pressure to give the crude product hydroxylamine 19, whichwas used without further purification because of its instability. The sample for structurecharacterization was purified by flash column chromatography on silica gel (petroleum ether/EtOAc= 5/1) as a colorless syrup.Data for (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2- ((benzyloxy)methyl)-1-hydroxyl-5-(oct-7-en-1-yl)pyrrolidine (19): [alpha]D 20 -8.6 (c 1.2 in CH2Cl2); numax/cm-1: 3030 (w), 2926 (s), 2855 (s), 1454 (m), 1362(w), 1097 (s), 735 (m), 697 (s); 1H-NMR (400 MHz, CDCl3) delta 7.32-7.24 (m, 15H), 5.80 (ddt, J = 16.9, 10.2,6.6 Hz, 1H), 5.01-4.91 (m, 2H), 4.56-4.42 (m, 6H), 3.95-3.92 (m, 1H), 3.80-3.76 (m, 2H), 3.58 (dd, J =9.2, 6.9 Hz, 1H), 3.54-3.50 (m, 1H), 3.17 (dt, J = 7.5, 5.4 Hz, 1H), 2.04-1.99 (m, 2H), 1.88-1.83 (m, 1H),1.50-1.43 (m, 1H), 1.42-1.28 (m, 8H); 13C-NMR (100 MHz, CDCl3) delta 139.3, 138.3, 138.2, 138.2, 128.5,128.5, 128.1, 128.0, 127.8, 127.8, 127.7, 114.3, 86.8, 84.7, 73.5, 71.8, 71.8, 70.2, 70.1, 68.4, 33.9, 29.8, 29.2,29.0, 26.7; HRMS(ESI) calcd for C34H44O4N+ [M + H]+ 530.32649, found 530.32565.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-1-octene, and friends who are interested can also refer to it.

Reference:
Article; Wu, Qing-Kun; Kinami, Kyoko; Kato, Atsushi; Li, Yi-Xian; Jia, Yue-Mei; Fleet, George W.J.; Yu, Chu-Yi; Molecules; vol. 24; 20; (2019);,
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Electric Literature of 53078-85-6, These common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, 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 solution of 2-bromo-5-methylaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at 00C under N2 atmosphere was added dropwise IM NaHMDS (2.5 eq.) The reaction was stirred for 15 minutes at 00C, and a solution of di-tert -butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-5% ethyl acetate in hexane to give product as light yellow oil.

The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
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These common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, 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. Safety of (2-Bromovinyl)benzene

An oven-dried vial equipped with a stir bar was dessicated. To a solution of CoBr2 (22 mg, 0.10 mmol, 10 mol%), bis-1,2-diphenylphosphinohexane (43.2 mg, 0.10 mmol, 10 mol%), and manganese powder (165 mg, 3 mmol, 3 equiv) in acetonitrile (5 mL) was added the alkenyl bromide (1.5 mmol, 1.5 equiv) at 50 oC. A solution of the chlorodehydropiperidine (1 mmol, 1 equiv) in acetonitrile (5 mL) was added slowly. After completion (as judged by TLC and GC-MS), the reaction mixture was treated with a mild acid such as 10% H3PO4 (aq) and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the desired coupling product as an oil. Purification was carried out by flash chromatography on silica (pretreated with 1% Et3N).

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

Reference:
Article; Farah, Abdikani Omar; Archibald, Ryan; Rodriguez, Morgan J.; Moreno, Antonio; Dondji, Blaise; Beng, Timothy K.; Tetrahedron Letters; vol. 59; 38; (2018); p. 3495 – 3498;,
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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. Recommanded Product: 1-Bromo-2,3-difluorobenzene

To a 500 mL three-necked flask equipped with a thermometer, a condenser and a magnetic stirrer were added 33.0 (0.21 mol) of 4-ethylbenzeneboronic acid, 38.6 g (0.20 mol) of 2,3-difluorobromobenzene, 58.0 g (0.42 mol) of potassium carbonate, 240 mL of N, N- dimethylformamide and 80 mL of H2O. The temperature was raised to 80¡ãC. After the solid was totally dissolved, 2.3g (2mmol) of tetrakis(triphenylphosphine)palladium was added and the reaction was carried out at 80 ¡ã C for 8 hours. The reaction mixture was diluted with petroleum ether and the organic phase was separated. The aqueous layer was extracted three times with petroleum ether The organic phase was combined and washed with water until neutral, dried over anhydrous magnesium sulfate, filtered and the solvent was distilled off under reduced pressure. A fraction of 110-115C / 40Pa was collected to obtain a colorless oil.

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

Reference:
Patent; Shaanxi Normal University; An, Zhongwei; Mo, Lingchao; Chen, Xinbing; Chen, Pei; (12 pag.)CN103214353; (2016); B;,
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Electric Literature of 2270-59-9, These common heterocyclic compound, 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, 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.

General procedure: Freshly activated and dried magnesium turnings (1.38 equiv relative to aldehyde) were weighed into a flame-dried round bottom flask equipped with a stir bar. The flask was purged with nitrogen, cooled to 0 C, and diethyl ether dispensed (to approximate concentration 0.6 mmol/mL). Seventy microliters 1,2-dibromoethane were added to activate the magnesium and stirred for 15 minutes. At 0 C, 5-bromo-2-methyl-2-pentene (1.25 equiv relative to aldehyde) was added dropwise to the stirring magnesium turnings and stirred for 2 hours (consumption of magnesium observed). After formation of the Grignard reagent, the necessary aldehyde (freshly distilled to ensure purity), in diethyl ether, was added to the reaction mixture dropwise at 0 C and stirred for 18 hours. The reaction was quenched with concentrated NH4Cl solution dropwise and diluted with DI water and diethyl ether. The organic layer was separated and aqueous layer extracted three times with diethyl ether in a separatory funnel. The combined organics were washed with brine, dried with anhydrous MgSO4, filtered, and concentrated to afford a crude oil, which was taken on to the next step without further purification

The synthetic route of 2270-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gesmundo, Nathan J.; Nicewicz, David A.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1272 – 1281;,
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These common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, 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. SDS of cas: 38573-88-5

Example 33 [0128] (4-(2-(2, 3-DIFLUOROPHENYL) ETHYNYL)-1-BOC-PYRROL-2-YL) (PYRROLIDIN-1- yl) methanone. A mixture of (4-ethynyl)-1-BOC-pyrrol-2-yl) (pyrrolidin-1-yl) methanone (4 g, 13. 88 mmol), 2, 3-DIFLUORO-1-BROMOBENZENE (4 g, 20.8 mmol), PDCL2PPH2 (0.97 g, 1. 38 mmol) and Cul (0.53 g, 2.76 mmol in trietylamine (40 ML) was stirred at room temperature for 4 hr. The solid was filtered and washed with ethyl acetate (100 mL). The filtrate was washed with 2N HC1 (3x 100 mL), brine (100 mL) and water (100 mL). The organic layer was dried and concentrated under reduced pressure. The crude product was purified by Biotage HPFC system (40-65percent EtOAC/Hexane) to afford title as a dark brown oil (1.35 g, 24percent).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LI, Pan; TOMLINSON, Ronald, C.; WO2005/16920; (2005); A1;,
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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. 1073-06-9, name is 1-Bromo-3-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H4BrF

To a solution of diisopropylamine (76 niL, 0.4 mol) in dry THF (664 mL) and n-hexane (220 mL) is added 2.5 M /?-BuLi (160 mL. 0.4 mol) dropwise at -780C during a period of 1 h. The mixture is stirred for 1 h at -780C. Then a solution of 1- bromo-3-fiuoro-benzene (69 g, 0.4 mol) in dry THF (300 mL) at -780C is added to the above mixture dropwise. After stirring for an additional 1 h at -780C, the mixture is added a solution of iodine (101 g, 0.4 mol) in dry THF (400 mL) dropwise at – 780C. The temperature is raised from -780C to rt during 2 h. After stirring for 18 h at rt, the mixture is concentrated in vacuo to give crude product (120 g) which is distilled under reduced pressure to afford l-bromo-3-fluoro-2-iodobenzene (110 g). 1H NMR (400MHz, DMSO): 7.24-7.19 (t, IH), 7.38-7.32 (m, IH), 7.55-7.53 (d, IH).

The synthetic route of 1073-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.; WO2008/124575; (2008); A1;,
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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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5BrFN

A solution of sodium nitrate (0.49g, 0.007mM) in water [(1.] [5ML)] was added drop wise to a vigorously stirred heterogeneous solution of [5-BROMO-2FLUOROANILINE] (1.4g) in concentrated HC (aq) (3. [5ML)] over a 30 minutes period at 0C. Tin [(II)] chloride [DIHYDRATE] (4. 5g, 0.02mM) in concentrated [HC .] (aq) (3. 5ml) was added drop wise to the above solution over a period of 30 minutes. After the addition, the solution was allowed to stir at [0C] for one hour. The reaction solution was basified (pH>7) by slowly adding a solution of 50% aqueous NaOH to the reaction mixture. The water layer was washed with diethyl ether (3x). The organic layers were combined, dried [(MGS04),] and concentrated. The resultant solid was thoroughly washed with hexanes. The undissolved solid was captured on filter and further washed with hexanes to afford [0.] [81 G] (54% yield) of the desired product as an off- white solid. NMR [(CHC13)] [8] 5.45 (bs, 1H) ; 6.80-6. 86 (m, 2H); 7.25-7. 28 [(M,] 1H). [[0085]] See, McKittrick, B. et al. , J. Heterocyclic Chem. 27,2151 (1990), hereby incorporated by reference.

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 2924-09-6.

Reference:
Patent; WYETH; VIROPHARMA INCORPORATED; WO2003/99824; (2003); A1;,
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