Category: 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. HPLC of Formula: C10H13BrO

[(3-Benzyloxy-propyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester: To an oven-dried flask was added 10.25 g (44.7 mmol) of (3-Bromo-propoxymethyl)-benzene and 7.67 mL (44.7 mmol) of triethyl phosphite. The flask was fitted with a short-path distillation head, for removal of bromoethane, and the mixture heated at 150° C. for 4 h. The reaction was cooled to ambient temperature, and then diluted with 120 mL of absolute ethanol and 1.8 N KOH (120 mL, 216 mol). The distillation head was replaced with a reflux condenser and the solution heated at reflux for 5 h. The reaction was cooled then concentrated in vacuo. The basic aqueous layer was extracted with EtOAc (2*) and then acidified to pH 3 with conc. HCl. The aqueous layer was extracted with EtOAc (3*) and the combined extracts were dried over MgSO4 and concentrated. The resulting crude product (8.24 g) was used as is in the next reaction. 31P NMR (300 MHz, DMSO-d6) delta34.113.

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

Reference:
Patent; Wang, Yihan; Metcalf III, Chester A.; Shakespeare, William C.; Sawyer, Tomi K.; Bohacek, Regine; US2003/100573; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. HPLC of Formula: C10H13BrO

Example 7.9 Preparation of (1S,5R,6R)-3-(3-(benzyloxy)propyl)-10-((3,5-dichlorophenyl)sulfonyl)-5-vinyl-3,10-diazabicyclo[4.3.1]decan-2-one J1 To a solution of (1S,5R,6R)-10-((3,5-dichlorophenyl)sulfonyl)-5-vinyl-3,10 – diazabicyclo [4.3.1] decan-2-one (35.0 mg, 0.0899 mmol) in DMF (1.0 mL) was added NaH (5.39 mg, 0.135 mmol). After 20 minutes ((3-bromopropoxy)methyl)benzene (20.6 mg, 0.0899 mmol) was added, the solution was heated to 80 °C and stirred for 1 h. Et2O (90 mL) was added to the solution and washed with sat. aq. NaCl solution (3 * 10 mL). The organic layer was dried over MgSO4 and the solvent removed under reduced pressure. Column chromatography on SiO2 (Cyclohexane/EtOAc = 1:1) afforded the title compound (31.0 mg, 0.0577 mmol, 64.2 percent) as a colorless solid. Rf: 0.25 (Cyclohexane/EtOAc = 7:3) 1H NMR (600 MHz, CDCl3) delta = 1.28 (s, 2 H), 1.47 – 1.54 (m, 3 H), 1.83 – 1.92 (m, 2 H), 2.23 – 2.29 (m, 1 H), 2.58 – 2.64 (m, 1 H), 2.95 – 3.00 (m, 1 H), 3.49 – 3.59 (m, 4 H), 3.95 – 4.04 (m, 2 H), 4.50 (s, 2 H), 4.65 (d, J = 6.2 Hz, 1 H), 5.09 – 5.15 (m, 2 H), 5.74 – 5.82 (m, 1 H), 7.28 (s, 1 H), 7.33 (d, J = 1.3 Hz, 4 H), 7.56 (s, 1 H), 7.69 (d, J =1.8Hz,2H). 13C NMR (150 MHz, CDCl3) delta = 15.42, 26.29, 26.89, 27.36, 28.14, 29.68, 49.16, 49.53, 51.85, 54.83, 56.84, 67.64, 73.08, 116.8, 124.9, 127.6, 127.7, 128.4, 132.6, 136.3, 137.2, 138.2, 144.1, 169.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54314-84-0, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., HPLC of Formula: C10H13BrO

Compound 38E: Methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)- 1 /-/-pyrrole-2-carboxylate.A mixture of methyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-2- carboxylate (Compound 38F, 600 mg, 2.39 mmol) and 1-bromo-3-benzyloxypropane (575 mg, 2.51 mmol) in DMF (2.19 mL) was charged with cesium carbonate (778 mg, 2.39 mmol). The reaction mixture was allowed to stir at 70 °C for 16 hrs. The reaction mixture was diluted with water and then extracted with EtOAc (2x). The organic layer was washed with water (2x), brine (1 x), dried over Na2S04, filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash.(R). Rf system [0–> 4percent Ethanol in DCM] to afford 442mg of the title compound (46percent). 1H NMR (400 MHz, CD3OD) delta 7.26 – 7.37 (m, 5H), 7.25 (d, J = 1 .8 Hz, 1 H), 7.17 (d, J = 1.8 Hz, 1 H), 4.45 (s, 2H), 4.42 (t, J = 6.8 Hz, 2H), 3.78 (s, 3H), 3.38 (t, J = 5.9 Hz, 2H), 2.01 (t, J = 6.2 Hz, 2H), 1 .31 (s, 12H). MS (ESI): m/z 440.59 [M+H]+. UPLC: tR = 1.60 min (UPLC-TOF: polar_2 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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

Intermediate 104a: diethyl 2-(3-(benzyloxy)propyl)malonate To a suspension of sodium hydride (1.05 g, 26 mmol) in tetrahydrofuran (40 mL), was added diethyl malonate (7g, 44 mmol). Once evolution of gas had ceased, ((3- bromopropxy)methyl)benzene (5 g, 22 mmol) was added. The reaction mixture was heated in a 90 deg C bath for 6 h, then cooled to ambient temperature. The reaction was diluted with diethyl ether (100 mL) and washed with water (100 mL). The aqueous layer was separated and extracted with diethyl ether (2 x 100 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica-gel chromatography with ethyl acetate and heptanes as eluent to provide the desired compound. H NMR (400 MHz, CDCI3) delta 7.31-7.38 (m, 4H), 7.25-7.31 (m, 1 H), 4.50 (s, 2H), 4.10-4.27 (m, 7H), 3.50 (t, =6.3 Hz, 2H), 3.32-3.41 (m, 2H), 1.93-2.08 (m, 2H), 1.60 – 1.73 (m, 2H), 1.20- 1.38 (m, 10H) ppm.

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

Reference:
Patent; NOVARTIS AG; BARYZA, Jeremy Lee; BECKWITH, Rohan Eric John; BOWMAN, Keith; BYERS, Crystal; FAZAL, Tanzina; GAMBER, Gabriel Grant; LEE, Cameron Chuck-Munn; TICHKULE, Ritesh Bhanudasji; VARGEESE, Chandra; WANG, Shuangxi; WEST, Laura; ZABAWA, Thomas; ZHAO, Junping; WO2014/136086; (2014); A1;,
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Ether | (C2H5)2O – PubChem

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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H13BrO

Magnesium (317.2 mg, 13.05 mmol) was suspended in 5 mL of ether, a solution of 2.30 mL (13.0 mmol) of 3-benzyloxypropyl bromide in 7 mL of ether was dropped into the suspension over 10 minutes, a flake of iodine was added thereto and the mixture was heated to reflux for 1 hour. The reaction mixture was cooled with an ice-methanol bath, a solution of 5.1 mg (0.011 mmol) of N-methoxy-N-methyl-(1-methylindole)-2-carboxamide in tetrahydrofuran was added thereto and the mixture was stirred at 0°C for 2 hours. Ice water was added to the reaction solution and the mixture was acidified with 6 mol/L hydrochloric acid and extracted with ether. The organic layer was washed with water and a saturated aqueous saline solutio dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate = 8/1) to give 0.79 g (54percent) of 2-(4-benzyloxy-1-oxobutyl)-1-methylindole.1H-NMR(270MHz, DMSO-d6, delta); 2.09(m, 2H), 3.10(t, J=7.3Hz, 2H), 3.58(t, J=6.1Hz, 2H), 4.05(s, 3H), 4.50(s, 2H), 7.15(m, 1H), 7.26-7.39(m, 8H), 7.69(dd, J=1.0Hz, 8.3Hz, 1H). Fab-MS(m/z); 308[M+1]+

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 54314-84-0.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1464645; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, 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 54314-84-0, category: ethers-buliding-blocks

Reference Example 9[4-(3-Benzyloxypropoxy)-2-methylphenyl]methanol To a solution of 4-bromo-3-methylphenol (2.5 g) inN,N-dimethylformamide (10 mL) were added cesium carbonate (4.79 g), benzyl 3-bromopropyl ether (2.48 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 60 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(3-benzyloxypropoxy)-1-bromo-2-methylbenzene. This material was dissolved in tetrahydrofuran (100 mL). To the solution was added n-butyl lithium (2.46 mol/Ln-hexane solution, 6 mL) at -78°C under an argon atmosphere, and the mixture was stirred for 5 minutes. To the reaction mixture was added N,N-dimethylformamide (2.57 mL), and the mixture was allowed to warm to 0°C and stirred for 1 hour. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(3-benzyloxypropoxy)-2-methylbenzaldehyde. This material was dissolved in ethanol (40 mL). To the solution was added sodium borohydride (506 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added methanol, and the resulting mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 5/1 – 1.5/1) to give the title compound (3.33 g).1HNMR (CDCl3) delta ppm: 1. 37 (1H, t, J=5.7Hz), 2.0-2.15 (2H, m), 2.36 (3H, s), 3. 66 (2H, t, J=6.2Hz), 4.08 (2H, t, J=6.3Hz), 4.52 (2H, s), 4.63 (2H, d, J=5.7Hz), 6.65-6.8 (2H, m), 7.15-7.4 (6H, m)

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; Kissei Pharmaceutical Co., Ltd.; EP1548024; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

Step A: methyl 2-cyanoacetate (23 g, 232 mmol) was addeddropwise to a suspension of sodium hydride (60percent, 2.79 g,69.7 mmol) in DMF (100 mL) and THF (100 mL) at 0 C, and thereaction mixture was warmed to rt and stirred at rt for 30 min.((2-Bromoethoxy)methyl)benzene (10 g, 46.5 mmol) was added,and the reaction mixture was stirred at rt for 12 h. Water wasadded and the aqueous layer was extracted with ether (3). Thecombined organic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was evaporatedto give the crude product. Excessive methyl 2-cyanoacetate wasremoved by distillation under high vacuum at 120?130 C, andremaining residue was purified by silica gel chromatography elutingwith 0?50percent EtOAc/hexanes to give methyl 4-(benzyloxy)-2-cyanobutanoate (8 g, 74percent) as a colorless liquid. 1H NMR(300 MHz, CDCl3) d 7.3 (m, 5H), 4.51 (s, 2H), 3.70 (s, 3H), 3.6?3.9(m, 3H), and 2.3 (m, 2H). LC/MS m/z: (M+H)+ calcd forC13H16NO3, 234.11; found 234.4. Step B: To a suspension of sodiumhydride (60percent, 9 g, 225 mmol) in THF (170 mL) and DMF (170 mL)was added methyl 4-(benzyloxy)-2-cyanobutanoate (35 g,150 mmol) at 0 C, and the reaction mixture was stirred at rt for30 min. ((3-Bromopropoxy)methyl)benzene (37.8 g, 165 mmol)was added, and the reaction mixture was stirred at rt for 12 h.Water was added and the aqueous layer was extracted with ether(3). The combined organic layers were washed with brine, driedover anhydrous sodium sulfate, and filtered, and the filtrate wasevaporated to give the crude product. The crude product was purifiedby silica gel chromatography eluting with 0?40percent EtOAc/hexanesto give 22 (40 g, 70percent) as a colorless oil. 1H NMR (400 MHz,CDCl3) d 7.3 (m, 10H), 4.48 (2H, s), 4.47 (2H, s), 3.7 (m, 2H), 3.57(3H, s), 3.48 (m, 1H), 2.42 (m, 1H), 1.8?2.1 (m, 4H), and 1.6 (m,1H). LC/MS m/z: (M+H)+ calcd for C23H28NO4, 382.20; found 382.4.

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; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. category: ethers-buliding-blocks

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;,
Ether – Wikipedia,
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Reference of 54314-84-0, These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)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.

Benzyl-3-bromopropyl ether(175 mL, 1.00 mmol) was dissolved in dimethylformamide(1 mL).N- (benzyloxycarbonyl) acetamide potassium salt(256 mg, 1.10 mmol), and the mixture was stirred at room temperature for 23 hours.The reaction was terminated by adding saturated aqueous ammonium chloride solution (about 3 mL)The reaction mixture was extracted with ethyl acetate.After washing the organic layer with water and saturated brine,And dried over anhydrous magnesium sulfate.Flash silica gel chromatography(10percent ethyl acetate / n-hexane)A colorless oil of N- (3- (benzyloxy) propyl) -N- (benzyloxycarbonyl) acetamide (311 mg, 91percent) was obtained.

Statistics shows that ((3-Bromopropoxy)methyl)benzene is playing an increasingly important role. we look forward to future research findings about 54314-84-0.

Reference:
Patent; School corporation Meijo University; Mori, Yuji; Sakai, Takeo; Fukuda, Ayumi; Kasai, Satomi; (28 pag.)JP2018/95576; (2018); A;,
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Ether | (C2H5)2O – PubChem

Application of 54314-84-0, 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. 54314-84-0 name is ((3-Bromopropoxy)methyl)benzene, 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.

Synthesized according to the methods of general procedure 4 in U.S. Pat. Pub. No. 20090227541 (U.S. Pat. App. No. 12/142,692) using the following reactants and amounts: 2-bromo-3-hydroxy-4-methoxy-benzaldehyde (1.0 g, 4.32 mmol), (3- bromo-propoxymethyl)-benzene (0.76 mL, 4.32 mmol), cesium carbonate (2.11 g, 6.5 mmol), DMF (30 mL). Purification: flash chromatography (10percent EtOAc/hexanes): yield 1.54 g (95percent). 1H NMR (400 MHz, CDC13) delta (ppm): 10.26 (s, 1 H), 7.73 (d, J=8.6 Hz, 1 H), 7.46-7.18 (m, 5 H), 6.95 (d, J=8.6 Hz, 1 H), 4.56 (s, 2 H), 4.14 (t, J=6.1 Hz, 2 H), 3.92 (s, 3 H), 3.77 (t, J=6.2 Hz, 2 H), 2.15 (quin, J=6.5 Hz, 2 H); MS (ESI): m/z = 381 (M+l, positive).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, ((3-Bromopropoxy)methyl)benzene, and friends who are interested can also refer to it.

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem