Tag: M.W=200-300

Reference of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

[00166] Intermediate 10A. (5-Bromo-2-methoxyphenyl)hydrazine: A suspension of 5-bromo-2-methoxyaniline (5.0 g, 25 mmol) in 6 M HC1 (13 mL) was cooled to -10 C and a solution of sodium nitrite (1.77 g, 26.0 mmol) in water (5 mL) was added slowly to keep the temperature below 0 C. After the addition, the reaction was stirred for an additional 20 min at -10 to 0 C. A solution of tin (II) chloride (14.1 g, 74.2 mmol) in cone. HC1 (25 mL) was added slowly, resulting in precipitation. The precipitate was filtered, suspended in 10% NaOH solution, and extracted with ether (3 x). The combined organics were dried over MgS04, filtered and evaporated to give Intermediate 10A (4.1 g, 76%) which was used directly in the next step. LCMS (ESI) m/z 200, 202 (M-NH3+H, M-NH3+2+H)+, RT = 1.01 min (Method A).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; L’HEUREUX, Alexandre; HIEBERT, Sheldon; HU, Carol; LAM, Patrick Y.S.; LLOYD, John; PI, Zulan; QIAO, Jennifer X.; THIBEAULT, Carl; TORA, George O.; YANG, Wu; WANG, Yufeng; WANG, Tammy C.; BOWSHER, Michael S.; RUEL, Rejean; WO2014/22343; (2014); A1;,
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Reference of 5467-58-3, The chemical industry reduces the impact on the environment during synthesis 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, I believe this compound will play a more active role in future production and life.

(0357) General procedure B: a mixture of 1-bromo-4-methoxynaphthalene (166 mg, 0.70 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (164 mg, 0.70 mmol), K2CO3 (290 mg, 2.10 mmol) and [Iota, – bis(diphenylphosphino)ferrocene]palladium(II) dichloride (29 mg, 0.04 mmol) in dioxane (10 mL) and H2O (2 mL) was heated at 100 C overnight in an atmosphere of nitrogen. The reaction was then quenched with water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (eluent: dichloromethane/methanol, 0-10%) to give the title compound as light yellow solid (143 mg, 77% yield). ESI-MS m/z: 263.1075 [M-H]”; Punty: 93.6%. (0358) 1H NMR (400 MHz, chloroform- ) delta 8.35- 8.28 (m, 1H), 7.91 – 7.84 (m, 1H), 7.52 – 7.40 (m, 2H), 7.30 (d, J = 7.9 Hz, 1H), 7.25- 7.21 (m, 1H), 7.18 (dd, J = 8.0, 2.2 Hz, 1H), 6.87 (t, J= 8.0 Hz, 2H), 4.04 (s, 3H), 2.33 (s, 3H). 13C NMR (101 MHz, CDC13) delta 154.82, 153.02, 133.56, 132.98, 132.84, 132.58, 129.03, 126.82, 126.50, 126.02, 125.81, 125.16, 123.58, 122.27, 114.83, 103.56, 55.71, 15.99.

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; YIN, Hang Hubert; ZHANG, Shuting; HU, Zhenyi; (114 pag.)WO2019/89648; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-Bromo-2-methoxyaniline, belongs to ethers-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 6358-77-6, Safety of 5-Bromo-2-methoxyaniline

Intermediate 20: Step a 4-Bromo-2-isothiocyanato-1-methoxy-benzene A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

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Reference:
Patent; JACKSON, Paul Francis; Tounge, Brett Andrew; Leonard, Kristi Anne; Zhang, Yan; Wang, Aihua; Hawkins, Michael; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129842; (2012); A1;,
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Electric Literature of 25245-34-5, 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. 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of sodium amide (8.5 g, 218 mmol) in anhydrous THF(100 mL) was added furan (59.3 g, 872 mmol) and the mixture warmed to 50 C under nitrogen. 4 (11 g,50.7 mmol) dissolved in anhydrous THF (20 mL) was added to the reaction mixture which was thenstirred at 50 C for 24 h. After cooled to room temperature, EtOAc (80 mL) and water (80 mL) wereadded to the solution. The organic layer was separated and washed with saturated aqueous NaCl and driedover anhydrous Na2SO4. The solvent was removed under reduced pressure to give a brown oil 5 withoutfurther purification which was dissolved in MeOH (100 mL) containing conc. hydrochloric acid (5 mL)and the mixture heated at reflux for 3 h. MeOH was removed under reduced pressure and the residue between EtOAc and water. The organic layer was washed with a solution of saturated aqueous NaHC03 and saturated aqueous NaCl in sequence and then dried over anhydrous Na2S04. The solvent was evaporated under reduced pressure and the residue was subjected to flash column chromatography (petroleum ether: EtOAc, 10:1, V/V) to give 6 (9.5 g, 91.3%) as white solid

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

Reference:
Article; Zhang, Qijing; Dong, Jinyun; Huang, Guang; Li, Shaoshun; Heterocycles; vol. 96; 2; (2018); p. 334 – 338;,
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These common heterocyclic compound, 52411-34-4, name is 1,2-Bis(o-aminophenoxy)ethane, 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 1,2-Bis(o-aminophenoxy)ethane

Diacetylpyridine (0.134 g, 0.82 mmol) was added in one portion to a solution of MnCl2-4H2O (0.142 g, 0.82 mmol) in EtOH (30 mL). The solution was heated to 50 C., and then 1,4-bis-(2-aminophenyl)-1,4-dioxabutane (0.200 g, 0.82 mmol) was added in one portion. The reaction mixture was heated to 85 C. and refluxed for 4 h. The solvent volume was reduced by half, and the mixture was cooled to r.t. An excess of Et2O was added, and the resulting precipitate was collected by Buchner filtration and washed well with cold Et2O to give 3 as an orange solid (62 mg, 14.2%). IR (cm-1) 3351, 3072, 2968, 2924, 1671, 1592, 1503, 1362, 1249, 1210, 1087. FAB-MS: m/z=461 [M-Cl]+ (10%). Anal. calcd. for (C23H21N3O2C1-2Mn)0-2H2O C, 55.55; H, 4.26; N, 8.45. found C, 55.72; H, 4.65; N, 8.39%

The synthetic route of 1,2-Bis(o-aminophenoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brock University; Pilkington, Melanie; Stares, Emma Louise; (51 pag.)US2016/362434; (2016); A1;,
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Synthetic Route of 156573-09-0, 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. 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Third Step 4-Bromo-2,3-difluoroethoxybenzene (s-5) (45.2 g), 2, 3-difluorophenyllboronic acid (s-6) (36.1 g), potassium carbonate (79.1 g), Pd (Ph3P)2Cl2 (4.0 g), toluene (200 ml), Solmix A-11 (200 ml) and water (200 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and heated to reflux for 2 hours. After the reaction solution had been cooled to 25C, it was poured into water (200 ml) and toluene (200 ml) and mixed with them. The mixture was then allowed to stand until it had separated into two layers of organic and aqueous layers, and the extraction into an organic layer was carried out. The resulting organic layers were separated, and washed with water, and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel as a stationary phase powder and a mixed solvent of toluene and heptane (toluene: heptane= 2:1 by volume) as an eluent, and further purified by recrystallization from Solmix A-11 and dried to give 4-ethoxy-2,2′,3,3′-tetrafluoro-1,1′-biphenyl (s-7) (40.1 g).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-ethoxy-2,3-difluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JNC Corporation; JNC Petrochemical Corporation; EP2479162; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, belongs to ethers-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 74137-36-3, category: ethers-buliding-blocks

Tris (dibenzylideneacetone) [DIPALLADIUM (0)] (6.53g, 7. [15MMOL)] was added in one portion to a stirred solution of the bromide of Preparation 1 (38. [0G,] [143MMOL),] 1,1′-bis (diphenylphosphino) ferrocene (9.3g, 16. [8MMOL)] and zinc cyanide (20. 0g, [172MMOL)] in [NN-DIMETHYLFORMAMIDE (300ML)] at room temperature under nitrogen. The reaction was heated at [100¡ãC] for 14 hours and cooled to room temperature. Water [(1500ML)] was added and the mixture was extracted with ethyl acetate [(3X500M1).] The combined organics were filtered and the filtrate was washed with water [(500MOI),] dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene [(1000MOL)] to provide the [TITLE COMPOUND (1 8. 0G)] as a tan solid. [1H-NMR] [(300MHZ,] [CDC13)] : [8] = 3.83 (3H, s), 7.31 (2H, s), 7.48 [(1 H,] s).

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Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); A1;,
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Application of 104197-14-0, 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 104197-14-0 as follows.

To a 200 mL flask which had been sufficiently dried under argon atmosphere, 30 mL of anhydrous pentane and 22.1 g (0.10 mol) of 4-bromo-2,6,-difluoroanisole were added and the mixture was cooled to -78 C. in a dry ice/acetone bath. Dropped thereto over 50 minutes was 61.2 mL of 1.6 mol/L n-butyl lithium hexane solution and the thus obtained mixture was subsequently stirred for 5 hours at -78 C. Thereto dropped over 30 minutes was 24.5 mL of 1 mol/L boron trichloride/hexane solution and the thus obtained reaction solution was stirred for 5 hours at -20 C. To this reaction solution, 80 mL of water was slowly added to hydrolyze the reaction mixture and the formed crystals were collected, which were then washed with 80 mL of hexane and 80 mL of water to obtain 13.0 g of tetrakis(3,5-difluoro-4-methoxyphenyl) lithium borate having an HPLC purity of 98.8% (Yield: 90%). The thus obtained product was subjected to measurements by 1H-NMR (heavy methanol solvent) and MALDI TOF-MS to confirm that it was the desired product. (Measurement Results)(1H-NMR (shift; ppm: multiplicity: number of protons)(3.8: s: 12) (6.5-6.6: m: 8)(0177)MALDI TOF-MS (m/z)mass: 583.25 (Theoretical value: 583.27)

According to the analysis of related databases, 104197-14-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Adeka Corporation; Kimura, Kentaro; Fujita, Shohei; Tamachi, Tomoya; US8383862; (2013); B2;,
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These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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. Quality Control of 4-Bromo-2-methoxyaniline

EXAMPLE 175B tert-butyl 4-bromo-2-methoxyphenylcarbamate A mixture of Example 175A (36.4 g, 180 mmol), and di-tert-butyl dicarbonate (47.2 g, 216 mmol) in THF (500 mL) was heated to reflux for 20 hours and cooled to ambient temperature. HPLC (using the conditions from Example 175A, product Rt=13.55 min and TLC (8:2 heptane/ethyl acetate, Rf of product=0.53, Rf of 4-bromo-2-methoxyaniline=0.27) indicated approximately 10% starting material was remaining. Additional di-tert-butyl dicarbonate (3.9 g, 18 mmol) was added and heating was continued for another 5 hours. The mixture was cooled and evaporated under reduced pressure. The residue was applied to a 400 gram silica gel column and eluted with 8:2 heptane/ethyl acetate. The fractions showing the desired product were combined and washed with saturated NaHCO3 and then brine. The organic solution was dried (MgSO4), filtered, and concentrated to provide 61.3 g of a mixture of the desired product and di-tert-butyl dicarbonate which was used directly in the next step.

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

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/43347; (2005); A1;,
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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 589-10-6 as follows. SDS of cas: 589-10-6

Example 101 N’-[1-imidazol-1-yl-1-[3-(2-phenoxyethoxy)thiophen-2-yl]methylidene]-N,N-dimethylhydrazine (compound No. 101) To a solution of methyl 3-hydroxythiophene-2-carboxylate (0.992 g, 6.27 mmol) in N,N-dimethylformamide (12 ml) were added beta-bromophenetole (1.268 g, 6.31 mmol) and potassium carbonate (1.059 g, 7.66 mmol), and the mixture was stirred at 80C for 4.5 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give methyl 3-(2-phenoxyethoxy)thiophene-2-carboxylate (1.624 g, 5.83 mmol, yield 93%).

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; EP2168951; (2010); A1;,
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