Tag: M.W=100-200

These common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-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. name: 1-Bromo-2,4-difluorobenzene

EXAMPLE 19 Preparation of 4-(2,4-difluorophenyl)-anisole from 4-methoxyphenylmagnesiumbromide and palladium chloride/triphenylphosphine (0.05percent) A suspension of magnesium turnings (1.54 g; 63.3 mmoles-Pometon) in tetrahydrofuran (16.02 g) was heated at 65¡ã C. under stirring and under nitrogen. Then, iodine (0.02 g) and, after 30 minutes, 4-bromoanisole (11.69 g; 62.5 mmoles), in 1 hour, were added to the reaction mixture. At the end of the addition, the reaction mixture was kept at 75¡ã C. for 1 hour and, then, decanted obtaining a solution of 4-methoxyphenylmagnesiumbromide (solution A). A mixture of 1-bromo-2,4-difluorobenzene (11.4 g; 59.1 mmoles), palladium chloride (0.00526 g; 0.0297 mmoles–Fluka) and triphenylphosphine (0.03088 g; 0.1177 mmoles–Fluka) was de-aerated by vacuum/nitrogen at 25¡ã C. The mixture was heated at 85¡ã C., kept under stirring for 15 minutes and, then, solution A was added in 3 hours. At the end of the addition, the reaction mixture was kept at 85¡ã C. for 30 minutes. After cooling at 60¡ã C., a solution of 37percent hydrochloric acid (2 ml) in water (10 ml) was added in 20 minutes. The mixture was cooled at 40¡ã C. and the phases were separated. The solvent of the organic phase was evaporated under reduced pressure obtaining the desired compound (98.5percent yield).

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

Reference:
Patent; Zambon Group S.p.A.; US5312975; (1994); A;,
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Related Products of 202865-83-6, 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. 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To an oven-dried 5 mL screw-capped vial, N-(5-chloroquinolin-8-yl)butyramide (1a) (75 mg, 0.3mmol), heptafluoroisopropyl iodide (178 mg, 0.60 mmol), Pd(OAc)2 (6.7 mg, 0.03 mmol),1-AdCOOH (10.8 mg, 0.06 mmol), K2CO3 (124 mg, 0.9 mmol), toluene (276 mg, 3.0 mmol) andchlorobenzene (0.7 mL) were added in a glove box. The mixture was stirred for 48 h at 140 Cfollowed by cooling. The resulting mixture was filtered through a celite pad and concentrated invacuo. The residue was purified by column chromatography on silica gel (eluent: hexane/EtOAc=2/1) to afford the desired alkylated product 2a (61 mg, 60%) as a white solid.

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-3-fluoro-5-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kubo, Teruhiko; Aihara, Yoshinori; Chatani, Naoto; Chemistry Letters; vol. 44; 10; (2015); p. 1365 – 1367;,
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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 4333-56-6 as follows. Product Details of 4333-56-6

To a stirred solution of cyclopropyl bromide (4.0 mL, 50 mmol) in 120 mL of ether at-78C was added dropwise a 1.7M solution of t-butyllithium in pentane (44.5 mL, 75.7 mmol). After 10 min, cooling bath was removed, stirring was continued for 1.5 h. The mixture was cooled again in a-78C bath, and 3-furaldehyde (3.5 mL, 41.9 mmol) was added. Reaction was continued for 1 h, and quenched with a saturated NH4CI aqueous solution. The aqueous mixture was extracted with CH2CI2 (100 mL x 3). The organic extracts were washed with brine, dried by Na2SO4, filtered, and concentrated in vacuo to give 5.3 g (91 %) of the alcohol product as a yellow oil.

According to the analysis of related databases, 4333-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2005/68460; (2005); A1;,
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Reference of 1647-23-0, These common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, 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.

4-Bromo-2-hydroxy pyridine (600mg, 3.4mmol)taken up in dry DMF under nitrogen. Sodium hydride 60% in oil (165mg, 4.lmmol) added and stirred 30 minutes. Lithiumbromide (598mg, 6.8mmol) added and stirred 1 hour. 1-Bromo-3,3-dimethyl butane (870uL, 6.8mmol) added and stirred 3 days. Reaction was reduced in vacuo and taken up in DCM. This was washed with water, iN NaOH then dried over magnesium sulfate filtered and reduced in vacuo to obtain 860 mg crude product to be used as is in next step. LRMS (ESI) m/z 258/260 [(M+H)], calc?d for C11H16BrNO: 258.16.

Statistics shows that 1-Bromo-3,3-dimethylbutane is playing an increasingly important role. we look forward to future research findings about 1647-23-0.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; GARDYAN, Michael Walter; GREEN, Michael Alan; GODWIN, Kumi; ZHANG, Yulian; WO2015/35167; (2015); A1;,
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1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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: 1647-26-3

Example 58A Di-tert-butyl {2-[6-(2-cyclohexylethoxy)-1-benzofur-3-yl]-2-oxoethyl}[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]malonate To a mixture of 300 mg (0.53 mmol) of the compound from Example 55A in 3 ml of acetonitrile were added at RT 221 mg (1.60 mmol) of potassium carbonate, followed by 306 mg (1.60 mmol) of 2-(bromoethyl)cyclohexane and the mixture was stirred under reflux for 4 h. After cooling to RT, the mixture was admixed with water and extracted twice with ethyl acetate. The combined organic phases were washed once with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. The residue was purified by means of column chromatography (40 g of silica gel, mobile phase: cyclohexane/ethyl acetate 85:15). 140 mg (37% of theory, purity 96%) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.71 min, m/z=674 [M+H]+.

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (120 pag.)US2017/121315; (2017); A1;,
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Electric Literature of 2695-48-9, 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. 2695-48-9, name is 8-Bromo-1-octene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Step 1) Anhydrous tetrahydrofuran (10 ml) was added to (4S,5R)-3,4-dimethyl-1-(5,5,6,6,7,7,8,8,8-nonafluoro-octanoyl) -5-phenylimidazolidin-2-one (1.20 g, 2.5 mmol) under nitrogen atmosphere, and the resulting mixture was cooled to -78 C. Lithium bis(trimethylsilyl)amide (2.75 ml, 1.0 M in tetrahydrofuran, 2.75 mmol) was added to the mixture, which was then stirred for 1 hour. After addition of 8-bromo-1-octene (714 mg, 3.0 mmol) and HMPA (1.25 ml) at -78 C., the reaction mixture was warmed with stirring up to -50 C. over 2 hours and up to 0 C. over 30 minutes, and then stirred for 12 hours at 0 C. The reaction mixture was quenched with saturated aqueous ammonium chloride at 0 C., and then extracted with a mixed solvent of ethyl acetate and n-hexane (3:7). The organic layer was washed sequentially with saturated aqueous potassium bisulfate, saturated aqueous sodium chloride, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure using an evaporator and the resulting residue was purified by silica gel column chromatography (Kanto Kagaku, silica gel 60 (spherical, neutral), 40-100 mum, eluent: ethyl acetate/n-hexane=1/5 3/7) to give (4S,5R)-3,4-dimethyl-1-[(2R)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-decenoyl]-5-phenylimidazolidin-2-one (1.37 g, Yield 93%). Optical purity: 95.5% de, as measured by HPLC (column: Daicel Chiralpack AD, phi0.46*25 cm, solvent: n-hexane/isopropanol=97/3, flow rate: 0.5 ml/min, detection wavelength: 206 nm) 1H-NMR (270 MHz, CDCl3): delta 7.32-7.13 (m, 5H), 5.87-5.72 (m, 1H), 5.34 (d, J=8.9 Hz, 1H), 5.02-4.91 (m, 2H), 4.10-3.86 (m, 2H), 2.84 (s, 3H), 2.19-1.08 (m, 16H), 0.82 (d, J=6.5 Hz, 3H).

The synthetic route of 8-Bromo-1-octene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jo, JaeChon; Kwon, HeeAn; Lim, HyunSuk; Choi, JaeYoung; Morikawa, Kazumi; Kanbe, Yoshitake; Nishimoto, Masahiro; Kim, MyungHwa; Nishimura, Yoshikazu; US2003/114524; (2003); A1;,
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Reference of 583-75-5, A common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

In a 100 mL RBF, 4-bromo-2-methylaniline (3.7 g, 20 mmol) and DIPEA (6.95 mL, 40 mmol) were combined with DMF (40 mL). The reaction wascooled to 0 C in an ice bath and cyclopropanecarbonyl chloride (2.1 g, 20 mmol) was added. The mixture was stirred at 0 C for 1 h. Water and EtOAc were added to separate the phases and the aqueous phase was extracted with EtOAc. The organic layers were combined, dried over Na2S04, filtered, and concentrated under reduced pressure to give the title compound as a white solid (4.76 g, 94%). NMR (400 MHz, CDCl3) delta ppm 7.85-7.72 (m, 1 H), 7.38-7.28 (m, 2H), 7.15-7.02 (m, l H), 2.27 (s, 3H), 1.57- 1.48 (m, 1 H), 1.10 (quint, J = 3.9 Hz, 2 H), 0.92-0.79 (m, 2H); MS ESI [M + H]+253.9, calcd for [C, ,H12BrNO+H]+254.0.

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; UNIVERSITY HEALTH NETWORK; LIU, Yong; PAULS, Heinz W.; LAUFER, Radoslaw; LI, Sze-Wan; SAMPSON, Peter Brent; FEHER, Miklos; NG, Grace; PATEL, Narendra Kumar B.; LANG, Yunhui; WO2014/75168; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, 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 38573-88-5, Computed Properties of C6H3BrF2

EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and 1-bromo-2,3-difluorobenzene (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1 H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).

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-2,3-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
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These common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, 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. Computed Properties of C5H9Br

General procedure: The alkyl bromide (1.0 equiv) was added to a solution of mercaptoaceticacid (1.0 equiv) in methanol (10.0 mL) and the resultingsolution stirred. Then a solution of NaOH (2.0 equiv) in methanol(5.0 mL)was added slowly, and the final mixturewas stirred at roomtemperature or heated to reflux until absence of the alkyl bromide(checked by TLC). The reaction mixture was concentrated in vacuo,diluted with H2O, and neutralized with 1 N HCl. Then the obtainedreaction mixture was extracted with EtOAc. The combined organicfractions were washed with brine, dried with Na2SO4, and concentratedin vacuo. Purification of the crude residue by column chromatography(petroleum ether/EtOAc) afforded the title compound.

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

Reference:
Article; Chen, Ying; Wu, Bolin; Hao, Yameng; Liu, Yunqi; Zhang, Zhili; Tian, Chao; Ning, Xianling; Guo, Ying; Liu, Junyi; Wang, Xiaowei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 420 – 433;,
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Related Products of 111721-75-6, These common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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 stirred solution of 2-bromo-3-fluoroaniline (CAS 111721-75-6, 9.50 g, 50.0 mmol, 1.00eq.) in an aqueous hydrochloric acid solution (12.5 mL conc. HCI in 80.0 mL of water, 150mmol, 3.00 eq.) was added dropwise a 2.5 M solution of sodium nitrite (20.0 mL, 50.0 mmol,1 .00 eq.) in water at a temperature of 0C. After complete addition, a 4.5 M solution of sodiumacetate in water (62.4 mL, 281 mmol, 5.62 eq.) was added via dropping funnel, followed bydropwise addition of ethyl-2-oxocyclopentanecarboxylate (CAS 611-10-9, 7.40 mL, 50.0 mmol,1.00 eq.). The resulting yellow suspension was maintained at 0 C for 15 minutes and thenwarmed to room temperature and stirred for 2 hours. The reaction mixture was extracted thricewith dichloromethane (100 mL each) and the combined organic extracts were dried overmagnesium sulfate, filtered and concentrated under reduced pressure to give the crudehydrazone as a red oil (18.1 g). The residue was dissolved in ethanol (50.0 mL, 1.00 M), afterwhich sulfuric acid (6.63 mL, 125 mmol, 2.50 eq.) was added dropwise. The dark orangesolution was heated at 95 C for 6 days and then cooled to room temperature. The dark brownsolution was poured onto ice/water (200 mL) and extracted thrice with dichloromethane (200mL each). The combined organic extracts were washed with saturated aqueous bicarbonatesolution (200 mL), dried over magnesium sulfate, filtered and concentrated under reducedpressure to give a brown solid. The residue was purified by flash column chromatography (0-30% ethyl acetate/hexane gradient) and then recrystallized from hot ethyl acetate/hexane (9:1)to give the title compound as a light yellow solid (8.35 g, 42%). Rf = 0.22 (15% ethyl acetate/hexane, UV).

Statistics shows that 2-Bromo-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 111721-75-6.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; WITTROCK, Sven; MCKINNEY, David; SERRANO-WU, Michael, H.; LEMKE, Chris; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; MCCARREN, Patrick, Ryan; HARVEY, Rebecca, Ann; (652 pag.)WO2019/96922; (2019); A1;,
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