Category: 54314-84-0

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 54314-84-0 as follows. Computed Properties of C10H13BrO

To a solution of – uoro- , – y roxy- enza e y e (11.15 g, 71.42 mmol) in anhydrous DMSO (88 mL) under nitrogen were added sequentially sodium t-butoxide (13.72 g, 142.84 mmol) and benzyl-3-bromopropyl ether (17.29 g, 78.56 mmol) and the reaction mixture stirred at rt for 18 h. The mixture was diluted with water (400 mL) and extracted with EtOAc (4×100 mL). The combined organic layer was washed with water and brine, dried over MgS04, filtered and concentrated in vacuo. Purification was completed by flash chromatography (20percent EtOAc / hexane). Yield 11.5 g (77 percent).1H NMR (400 MHz, CHLOROFORM-^) delta ppm 11.62 (s, 1 H), 10.23 (s, 1 H), 7.42 – 7.16 (m, 5 H), 7.05 (dd, J=8.8, 5.3 Hz, 1 H), 6.54 (t, J=9.6 Hz, 1 H), 4.52 (s, 2 H), 4.13 (t, J=6.3 Hz, 2 H), 3.68 (t, J=6.1 Hz, 2 H), 2.12 (quin, J=6.2 Hz, 2 H). 19F NMR (376 MHz, CHLOROFORM- d): -132 ppm.

According to the analysis of related databases, 54314-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; DING, Charles; PLATTNER, Jacob, J.; ALLEY, Michael Richard, Kevin; ROCK, Fernando; ZHANG, Suoming; EASOM, Eric; LI, Xianfeng; ZHOU, Ding; WO2012/33858; (2012); A2;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., name: ((3-Bromopropoxy)methyl)benzene

Compound 3F: 1 -[3-(Benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H- pyrazoleA mixture of 4-(4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1 /-/-pyrazole (5.0 g, 26 mmol), potassium carbonate (4.27 g, 30.9 mmol) and 1-bromo-3-benzyloxypropane (6.20 g, 27.0 mmol) in DMF (20 mL) was stirred at 80 °C overnight, quenched with water (20 mL) and extracted with EtOAc (100 mL). The organic layer was washed with water (2 x 30 mL), brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ISCO system: EtOAc/Heptane = 30- 70percent) to afford 7.67 g of the title compound as a light-yellow oil (87percent). 1H NMR (CDCI3, 400 MHz): delta = 7.80 (s, 1 H), 7.66 (s, 1 H), 7.30-7.36 (m, 5H), 4.48 (s, 2H), 4.28 (t, J = 6.8 Hz, 2H), 3.43 (t, J = 5.8 Hz, 2H), 2.17 (m, 2H), 1.33 (s, 12H). MS (ES+): m/z = 343.36 [MH+]. HPLC: iR = 4.20 min ( ZQ3: polar_5 min).

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; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); A1;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., SDS of cas: 54314-84-0

To a solution of methyl isobutyrate 23 (5g, 49 mmol) in THF was added slowly a solution of LDA (52 mmol, generated from n-BuLi and diisopropyl amine) in THF at -78 0C, the reaction was stirred for 20 minutes. The resulting solution was treated with a solution of Benzyl 3-bromopropyl ether 22 in HMPA and stirred at -78 0C for 12 h, aq. HCI (1 N) was added and the resulting mixture extracted with ether, Organic layer washed with water, saturated NaHCO3, dried and concentrated, it was purified by to give the desired ester 24 (11.6 g, 80percent). 1HNMR (CDCI3) delta 7.36-7.26 (m, 5H), 4.49 (s, 2H), 3.65 (s, 3H), 3.45 (t, J = 6.5 Hz, 2H), 1.62-1.52 (m, 4H), 1.18 (s, 6H); 13C NMR (CDCI3) delta 178.3, 138.5, 128.3, 127.6, 127.5, 72.8, 70.5, 51.7, 42.0, 37.1 , 25.3, 25.1.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/158381; (2009); A1;,
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Synthetic Route of 54314-84-0,Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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 suspension of 4-chloro-3-hydroxy-5-nitrobenzamide (30 g, 139 mmol) and potassium carbonate (57.4 g, 416 mmol) in DMF (200 mL) under nitrogen was added at room temperature a solution of ((3-bromopropoxy)methyl)benzene (47.6 g, 208 mmol) dropwise during 1 minute. The reaction mixture was stirred at 80 °C overnight. The reaction mixture was cooled to room temperature and quenched by the addition of 200 mL of water. The aqueous phase was then extracted with DCM (3×100 mL). The combined organic layer was washed with water (4×200 mL) and brine (200 mL), dried, and concentrated under vacuum. The crude product was purified by silica gel chromatography (100 g column, 1:2 petroleum ether/EtOAc). The appropriate fractions were pooled and concentrated to afford 3-(3-(benzyloxy)propoxy)-4-chloro-5-nitrobenzamide (33 g, 90 mmol, 65.3percent yield) as a yellow solid. LCMS (m/z): 365 [M + H]+.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; FOSBENNER, David T.; GRAYBILL, Todd L.; KANG, Jianxing; KING, Bryan W.; LAN, Yunfeng; LEISTER, Lara Kathryn; MAHAJAN, Mukesh K.; MEHLMANN, John F.; MORALES-RAMOS, Angel I.; PESIRIDIS, George Scott; RAMANJULU, Joshi M.; ROMANO, Joseph J.; ROMERIL, Stuart Paul; SCHULZ, Mark J.; ZHOU, Huiqiang; (372 pag.)WO2019/69270; (2019); A1;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., SDS of cas: 54314-84-0

General procedure: Under an argon atmosphere,methyl 2-(4-hydroxyphenyl)acetate (3.51 g, 21.14 mmol) and caesium carbonate (13.78 g, 42.28 mmol)were suspended in dimethylformamide (130 mL), the mixture was stirred at ambient temperaturefor 2 h. Benzyl-2-bromoethylether (5.00 g, 23.25 mmol) was added and it was stirred at ambienttemperature for further 12 h. Water (250 mL) and ethyl acetate (250 mL) were added and the resultingphases separated. The organic phase was dried over sodium sulfate and concentrated in vacuum.Purification by chromatography on silica gel (gradient: 0?100percent ethyl acetate in cyclohexane) affordedthe title compound 8a as a white solid (5.30 g, 84percent yield)

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:
Article; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: ((3-Bromopropoxy)methyl)benzene

To a suspension of NaH (55 wt percent in oil, 253 mg, 5.8 mmol) in DMF (12 mL) was added 3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine (9) (1.4 g, 5.1 mmol) in DMF (12 mL) at 0 °C. After stirring for 10 min at room temperature, the mixture was cooled to 0 °C, and then benzyl 3-bromopropyl ether (1.37 g, 5.8 mmol) was added. The mixture was stirred for 1 h at room temperature, then 10percent aq NH4Cl and ethyl acetate were added to the reaction mixture. The mixture was extracted with ethyl acetate 2 times, and the combined extracts were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The residual paste was chromatographed on silica gel (AcOEt/hexane) to afford (10) as a colorless oil (1.71 g, 79percent yield).1H NMR (CDCl3, delta ppm): 6.85-7.47 (12H, m), 4.43 (2H, s), 3.80 (2H, t, J = 6.4 Hz), 3.46 (2H, t, J = 6.0 Hz), 2.92-3.10 (4H, m), 1.77-1.92 (2H, m).

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:
Article; Kubota, Katsumi; Kurebayashi, Hirotaka; Miyachi, Hirotaka; Tobe, Masanori; Onishi, Masako; Isobe, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 3005 – 3021;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

To a mixture of 1-(2-hydroxyethyl)-4-[2-(4-hydroxyphenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-indazole (2 g), cesium carbonate (1.64 g) and sodium iodide (0.38g) in N,N-dimethylformamide (10 mL) was added benzyl 3-bromopropyl ether (0.86 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (15 mL). To the solution were added triethylamine (1.22 mL) and pivaloyl chloride (0.93 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 3/1) to give 4-{2-[4-(3-benzyloxypropoxy)phenyl]ethyl}-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1-(2-pivaloyloxyethyl)-1H-indazole (2.11 g). This material was dissolved in ethyl acetate (20 mL). To the solution was added 10percent palladium-carbon powder (0.5 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 2/1 – 1/1) to give the title compound (1.59 g). 1H-NMR (CDCl3) delta ppm: 1.02 (9H, s), 1.03 (9H, s), 1.13 (9H, s), 1.15 (9H, s), 1.17 (9H, s), 2.0-2.1 (2H, m), 2.8-2.9 (1H, m), 2.9-3.0 (1H, m), 3.0-3.15 (1H, m), 3.2-3.3 (1H, m), 3.8-3.9 (2H, m), 3.9-4.0 (1H, m), 4.05-4.2 (3H, m), 4.21 (1H, dd, J=12.4Hz, 1.6Hz), 4. 3-4. 5 (4H, m), 5.2-5.3 (1H, m), 5.35-5.55 (2H, m), 6.05 (1H, d, J=7.8Hz), 6.64 (1H, d, J=6.9Hz), 6.75-6.85 (2H, m), 7.0-7.1 (3H, m), 7.15-7.2 (1H, m)

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; Kissei Pharmaceutical Co., Ltd.; EP1724278; (2006); A1;,
Ether – Wikipedia,
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Synthetic Route of 54314-84-0,Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

26.1.N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamideA mixture of 1 g (3.84 mmol) of 6-chloro-N-cyclopentylpyridine-3-sulfonamide, 1.32 g (9.59 mmol) of K2CO3 and 0.88 mL (4.99 mmol) of [(3-bromopropoxy)methyl]benzene in 8 mL of anhydrous DMF is heated for 12 hours at 40° C.After cooling to room temperature, the medium is taken up in 300 mL of EtOAc, washed successively with water (2*100 mL), saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10percent EtOAc.1.65 g of N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamide are thus obtained in the form of an oil.Yield=99percent.1H NMR, CDCl3, 400 MHz, delta (ppm): 8.85 (s, 1H); 8.1 (d, 1H); 7.5 (d, 1H); 7.4-7.3 (m, 5H); 4.5 (s, 2H); 4.2 (m, 1H); 3.6 (t, 2H); 3.2 (dd, 2H); 2.1 (m, 2H); 1.6-1.3 (m, 8H)

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; US2011/294788; (2011); A1;,
Ether – Wikipedia,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 54314-84-0

The reaction mixture of 28 (0.50 g, 1.5 mmol) and [(3-bromopropoxy)methyl]benzene (32) (0.44 ml, 2.5 mmol) in dry 1,4-dioxane (16 ml) was stirred for 5 days to afford the title compound as a white solid in 73% yield (0.62 g). mp: 228-229 C; 1H-NMR (400 MHz, DMSO-d6): delta = 7.27-7.40 (m, 15H), 6.76 (s, 1H), 5.21 (br, 1H), 4.46 (s, 2H), 3.85 (m, 1H), 3.46 (t, J = 5.8 Hz 2H), 3.21-3.39 (m, 6H), 3.03 (m, 1H), 2.25 (m, 1H), 1.49-1.95 (m, 6H); 13C-NMR (500 MHz, DMSO-d6): delta = 172.8, 158.9, 143.6, 143.5, 130.1, 128.5, 128.4, 128.2, 128.1, 127.6, 127.5, 121.1, 115.0, 81.3, 69.1, 67.0, 63.0, 59.8, 54.1, 53.2, 26.2, 23.9, 20.9, 19.0, 18.1; HRMS calcd. for C31H36N1O4 [M]+: 486.2644; found: m/z = 486.2663; HPLC (Method B): tR (min) = 15.2 (98%).

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:
Article; Yamashita, Yasunobu; Tanaka, Ken-ichiro; Yamakawa; Asano; Kanda, Yuki; Takafuji; Kawahara, Masahiro; Takenaga, Mitsuko; Fukunishi, Yoshifumi; Mizushima; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3339 – 3346;,
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Related Products of 54314-84-0, 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 210.2 (9.9 g, 34.82 mmol, 1.00 equiv), N,N-dimethylformamide (200 mL). This was followed by the addition of NaH (1.25 g, 52.08 mmol, 1.50 equiv) at 0° C. in a water/ice bath. The mixture was stirred for 1 h at 0° C. To this was added [(3-bromopropoxy) methyl] benzene (11.92 g, 52.03 mmol, 1.50 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 200 mL of NH4Cl (aq). The resulting solution was extracted with 2×300 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:15). This resulted in 3.3 g (22percent) of 210.3 as yellow oil.

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, ((3-Bromopropoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
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