Category: 1462-37-9

1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-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. 1462-37-9

After flushing the interior of the vessel with nitrogen, under nitrogen, 8.41 g (210 mmol) of sodium hydride (oily) and 80 ml of dry tetrahydrofuran were added to a 1000 ml four-necked flask, and while cooling with an ice-water bath, 34.00 g (100 mmol) in 350 ml of tetrahydrofuran was added dropwise. Immediately after the dropwise addition of DCMI in tetrahydrofuran solution, bubbles that appeared to be H 2 were observed. After foaming subsided, the temperature was raised to room temperature and stirred for 1 hour. Thereafter, while cooling the flask again with an ice-water bath, a solution of 50.01 g (233 mmol) of benzyl-2-bromoethyl ether dissolved in 50 ml of dry THF was added dropwise. After the dropwise addition, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes, then heated to 60 to 70 ¡ã C. and stirred for 18 hours. On the way, heating was stopped when benzyl-2-bromoethyl ether became a trace amount and consumption ceased almost at a time-dependent change by TLC.As a post-treatment, the flask was cooled with ice with stirring under nitrogen, 150 ml of ethyl acetate was added to the flask, then 100 ml of water was slowly added dropwise, the aqueous phase was separated off and the organic phase was washed with 100 ml of water For 2 times. The organic phase was concentrated with an evaporator to obtain 68.10 g of a viscous liquid with a yellowish tinge. Thereafter, silica gel column purification was carried out using a mixed solvent of hexane and ethyl acetate (hexane / ethyl acetate = 10/1 to 1/1 (volume ratio)), and the solvent was distilled off under reduced pressure to give the following compound 6 46.36 g (76.2 mmol: yield 76.2percent) was obtained as a viscous liquid.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; Machine: Mitsubishi ChemicalsCo ., Ltd .; Imai Nao Akira; Saito Yasuyo; Kawakami Kotoku; Fuji Tsuu Akira; (94 pag.)JP2017/222625; (2017); A;,
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1462-37-9, The chemical industry reduces the impact on the environment during synthesis 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, I believe this compound will play a more active role in future production and life.

step Bl – Ethyl phenylcyanoacetate (22, 18.3 mL, 0.1054 mol, Ar1 = Ph) was added dropwise to a suspension of NaH (4.85 g, 0.1213 mol, 60percent dispersion in oil) in DMF (200 mL) cooled to 0 C. The resulting mixture was stirred at 0 C for 30 min then benzyl 2-bromoethyl ether (20 mL, 0.1265 mmol) was added. The reaction mixture was then stirred at 60 C overnight, cooled to RT and partitioned between EtOAc and a saturated aqueous NH4Cl. The aqueous layer was thrice back- extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by Si?2 chromatography eluting with a EtOAc/hexane gradient (5 to 95percent EtOAc) to afford 20 g (60percent) of 24a.

The chemical industry reduces the impact on the environment during synthesis ((2-Bromoethoxy)methyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LEMOINE, Remy; MELVILLE, Chris Richard; ROTSTEIN, David Mark; WANNER, Jutta; WO2008/34731; (2008); A1;,
Ether – Wikipedia,
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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-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. 1462-37-9

To a stirred solution of 3,5-dimethyl lH-pyrazole-3,5-dicarboxylate (10 g, 54.30 mmol, 1 equiv.) and [(2-bromoethoxy)methyl] benzene (12.8 g, 59.51 mmol, 1.096 equiv.) in MeCN (200 mL) was added K2CO3 (11.3 g, 81.46 mmol, 1.5 equiv.) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 4 h at 90 ¡ãC. The mixture was allowed to cool down to room temperature and then quenched with water. The resulting mixture was extracted with EtOAc and the combined organic layers were dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluting with PE/EtOAc (10: 1) to afford the title compound as a yellow oil in 96.22percent yield.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
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1462-37-9, These common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)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.

Step b: Ethyl 1 -(2-(benzyloxy)ethyl)-4-(terf-butyldimethylsilyloxy)cyclohexanecarboxylate; [00165] To a mixture of the compound of Step a (102 g, 0.357mol) in THF (800 mL) at -78 0C was added lithium bis(tritnethylsiyl)amide (438 mL) dropwise under nitrogen. The mixture was stirred for 30 min followed by the addition of benzyl 2-bromoethyl ether (109 mL, 0.375mol). After stirring the mixture for another 30min at -78 ¡ãC, the reaction mixture was allowed to warm up to room temperature and stirred for 1 h. The mixture was diluted with ethyl acetate (1,000 mL) and washed with brine (1,000 mL), dried over Na2SO4 and filtered. The filtrate was concentrated to give a crude product which was purified by flash chromatography (silica gel, EtOAc/Hexane: 0/1 to 1/1) to give the ester-benzylether as a colorless oil (1 15 g, 73percent).

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 1462-37-9.

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
Ether – Wikipedia,
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1462-37-9, A common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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: To a suspension of NaH (688 mg, 27.8 mmol) in THF (80 mL) was added diethyl malonate (7.45 g, 46.5 mmol) dropwise. Then ((2-bromoethoxy)methyl)benzene (5 g, 23.2 mmol) was added. The reaction was heated to 90 ¡ãC for 5 hours. After cooling to room temperature, the mixture was diluted with EtOAc (50 mL), washed with water (50 mL x 2), dried over anhydrous Na2S04 and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with a gradient of 10percent – 30percent EtOAc/hexanes to to afford diethyl 2-(2-(benzyloxy)ethyl)malonate (6.6 g, 22.5 mmol, 81percent yield) as a colorless oil.

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; YUK, Inn H.; PURKEY, Hans; O’BRIEN, Thomas; WO2015/142903; (2015); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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 methyl 2-cyanoacetate (0.89 mL, 10.1 mmol) inDMF (20 mL) at rt was added sodium hydride (0.97 g, 24.2 mmol),and the reaction mixture was stirred at rt for 15 min. Tetrabutylammoniumiodide (0.37 g, 1.0 mmol) and ((2-bromoethoxy)methyl)benzene (3.35 mL, 21.19 mmol) were added, and the reactionmixture was stirred at 90 C for 3 h. Water was added and theaqueous layer was extracted with ether (3). The combinedorganic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was concentrated togive the crude product. The crude product was purified by silicagel chromatography eluting with 0?30percent EtOAc/hexanes to give14 (2.4 g, 65percent yield) as a colorless oil. 1H NMR (500 MHz, CDCl3)d 7.41?7.27 (m, 10H), 4.49 (s, 4H), 3.78?3.69 (m, 5H), 3.45 (s,3H), 2.49?2.40 (m, 2H), 2.06 (dt, J = 14.2, 4.7 Hz, 2H). LC/MS m/z:(M+H)+ calcd for C22H26NO4, 368.19; found 368.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1462-37-9, its application will become more common.

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

1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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 1. 4-(l-(2-(Benzyloxy)ethyl)-4-(trifluoromethyl)-lH-imidazol-2-yl)benzonitrile (0931) [00299] A mixture of Intermediate B-20 (1 g, 4.22 mmol), ((2-bromoethoxy)methyl)benzene (1.09 g, 5.07 mmol) and cesium carbonate (2.75 g, 8.44 mmol) in DMF (15 mL) was stirred for 18 h at 110 ¡ãC. After cooling to ambient temperature, the reaction mixture was poured into water (100 mL) and was then extracted with EtOAc (2 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 1.5 g (96percent) of 4-(l-(2-(benzyloxy)ethyl)-4-(trifluoromethyl)-lH-imidazol-2- yl)benzonitrile as a colorless oil. MS (ESI) m/z 371.8 [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 ((2-Bromoethoxy)methyl)benzene, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)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 1462-37-9, 1462-37-9

Example 38d methyl 3-(2-(benzyloxy)ethoxy)-5-methoxybenzoate To a solution of methyl 3-hydroxy-5-methoxybenzoate (Chakraporty, T. K. and Reddy, G. V. J. Org. Chem., 57, 1992, 5462.) (3.3 g, 18.1 mmol) in dry DMF (30 mL) was added K2CO3 (6.3 g, 45.3 mmol) at room temperature. The reaction was stirred at room temperature for 10 minutes then ((2-bromoethoxy)methyl)benzene (3.4 mL, 21.7 mmol) was added and the mixture stirred at 160 C. for 2 hrs. The reaction was cooled down to room temperature and diluted with EtOAc, washed with water and brine, and dried over MgSO4, filtered and concentrated to give the crude product (90%) which was used in the next step without further purification.

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

Reference:
Patent; SENOMYX, INC.; US2012/41078; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem