Category: 588-63-6

Electric Literature of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

General procedure: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole (L1): A solution of 3,5-dimethyl-1H-pyrazole (0.30 g, 3.2 mmol) in DMF/THF (v/v = 1:1, 12 mL) was added to a suspension of NaH (0.15 g, 6.4 mmol) in DMF/THF (v/v = 2:1, 15 mL) and stirred at 60 °C for 2 h. Then, the resulting solution was added under stirring to a solution of 3-bromopropyl phenyl ether (0.70 g, 3.2 mmol) in DMF (7 mL). The mixture was allowed to stir for 24 h at 60 °C, cooled, and treated cautiously with H2O (5 mL) to decompose excess NaH. The solvents were then evaporated under reduced pressure. The residue was extracted with ethyl acetate (3 * 15 mL), washed with H2O (2 * 15 mL). The organic phase was dried over MgSO4 and filtered, before the solvent was evaporated under reduced pressure. After workup and purification by chromatographic column on silica gel (hexane/ethyl acetate, 90:10), L1 was obtained as a colorless oil (0.47 g, 64percent).

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)benzene, its application will become more common.

Reference:
Article; Ulbrich, Ana H.D.P.S.; Campedelli, Roberta R.; Milani, Jorge L. Sonego; Santos, Joao H.Z. Dos; Casagrande, Osvaldo De L.; Applied Catalysis A: General; vol. 453; (2013); p. 280 – 286;,
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Synthetic Route of 588-63-6, A common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

a) 6-Bromo-3-(3-phenoxy-propoxy)-pyridine-2-carboxylic acid methyl esterA mixture of -bromo-3-hydroxypicolinic acid methyl ester (lOOmg, 0.43 mmol), sodium hydride (60percent dispersion in mineral oil) (17.3mg, 0.43 mmol), 3-phenoxypropyl bromide(68 muL, 0.43 mmol), in dimethyl acetamide (1.5 mL) was heated at 9O0C for 3 hours. The reaction was allowed to cool, poured onto water and then extracted with ethyl acetate (2 x3mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by silica chromatography eluting with 100percent petroleum ether to 30percent ethyl acetate/petroleum ether to obtain a white solid (95mg, 60percent). 1H NMR (300 MHz,CDCl3) delta: 7.48 (IH, d), 7.24-7.21 (3H, m), 6.91-6.86 (3H, m), 4.19 (2H, t), 4.15 (2H, t),3.88 (3H, s), 2.30-2.22 (2H, m).

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; WO2009/39553; (2009); A1;,
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588-63-6, name is (3-Bromopropoxy)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. Product Details of 588-63-6

The 148mgNa dissolved in 20ml of absolute ethanol until complete dissolution, 6-(3,5-difluoro)benzyl-2-thiouracil 234mg (0.92mmol) and 1- (3-bromo-propoxy) benzene 297mg (1.38mmol) was added thereto, TLC the reaction was complete after stirring overnight at room temperature; column chromatography, P:E = 5:1,2:1,1:1, the final product was 222mg, as a white solid, a yield of 62.14percent

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University; Zhang, Liang; FU, YUHONG; Qin, Hua; Wang, Xiao Wei; Liu, Jun Yi; (30 pag.)CN103864699; (2016); B;,
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Related Products of 588-63-6, These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

General procedure: Maslinic acid (MA, 1equiv) was dissolved in dry DMF (5mL), and finely grounded potassium carbonate (5 equiv) was added. After 60min of stirring at room temperature, the corresponding alkyl or benzyl bromide (2equiv) was added, and stirring was continued for 18h. The mixture was poured into an ice cold aq. HCl (5percent, 50mL), and the white precipitate was filtered off. Chromatographic purification (silica gel, hexane/ethyl acetate, 7:3) and recrystallization (ethanol) afforded the product.

Statistics shows that (3-Bromopropoxy)benzene is playing an increasingly important role. we look forward to future research findings about 588-63-6.

Reference:
Article; Siewert, Bianka; Pianowski, Elke; Obernauer, Anja; Csuk, Rene?; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 594 – 615;,
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These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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. Recommanded Product: 588-63-6

General procedure: Bromoethane (0.45 mL, 6 mmol) was dropped to the mixture of 8 (0.86 g, 3 mmol), K2CO3 (0.83 g, 6 mmol) and KI (catalytic amount) in CH3CN. The mixture was stirred at 35°C for 8 h. he reaction mixture was filtered. The filtrate was concentrated and purified by chromatography on a silica gel column, eluting with a mixture of ethyl acetate and petroleum ether to give the desired product. 4.1.4.23. (E)-Ethyl 3-{5-[(biphenyl-4-ylmethyl)(3-phenoxypropyl)amino]methyl}furan-2-ylacrylate (12i). Compound 12i (1.29 g, 86.6percent yield) was synthesized from 11 (1.26 g, 3 mmol) and (3-bromopropoxy)benzene (0.77 g, 3.6 mmol) according to the procedure used to synthesize 9a; oil; MS (EI) m/z 495 (M+).

The synthetic route of (3-Bromopropoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Taotao; Wang, Hai; Su, Hong; Lu, Hui; Yu, Liqin; Zhang, Xiaojin; Sun, Haopeng; You, Qidong; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5339 – 5354;,
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Reference of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

[0187] Into a 5 L 3-necked roundbottom flask, was placed a solution of l-(3- bromopropoxy)benzene (250 g, 1.16 mol) in THF (600 ml). To this was added dimethylamine in water (1 L 33percent). To the mixture was added KOH (200 g, 4.46 mol). The resulting solution was allowed to react, with stirring, for 5 hours while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (EtOAc/PE = 1 :3). The resulting solution was extracted five times with 200 ml of EtOAc and the organic layers combined. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 20Og of crude N,N-dimethyl-3-phenoxypropan-l -amine as light yellow oil.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); A1;,
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Reference of 588-63-6, A common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

tert-BuLi (12 mL of a 1.7 M solution, 20 mmol) was added dropwise to a solution of 4-bromo-N,N-dimethylaniline (2.00 g, 10 mmol) in THF (40 mL) at 78° C. The resulting solution was stirred at 78° C. for 1 hour and was then warmed to ambient temperature. Tellurium powder (1.28 g, 10 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 1 hour. 1-Bromo-3-phenoxypropane (2.04 g, 9.5 mmol) in 5 mL of THF was added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was filtered through Celite and the filter cake was washed with CH2Cl2 (50 mL). The filtrate was concentrated and the residue was partitioned between H2O (100 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted with additional CH2Cl2 (3*25 mL). The combined organic extracts were dried over MgSO4 and concentrated. The crude product was then purified by column chromatography on silica gel eluted with 60percent CH2Cl2/hexanes to give 1.9 g (52percent) of 23b as an orange oil: 1H NMR (400 MHz, CDCl3) 7.63 (d, 2H, J=8.8 Hz), 7.24 (t, 2H, J=7.8), 6.91 (t, 1H, J=7.2), 6.84 (d, 2H, J=8.0 Hz), 6.54 (d, 2H, J=8.8 Hz), 3.97 (t, 2H, J=6.0 Hz), 2.94 (s, 6H), 2.90 (t, 2H, J=7.4 Hz), 2.20 (quint, 2H, J=6.8 Hz); 13C NMR (75 MHz, CDCl3) delta 158.9, 150.3, 141.2, 129.4, 120.6, 114.5, 113.4, 94.7, 68.7, 40.2, 31.2, 4.3; High Resolution MS (EI) m/z 385.0694 (Calcd for C17H21NO130 Te: 385.0681). Anal. Calcd for C17H21NOTe: C, 53.32; H, 5.53; N, 3.66. Found: C, 53.26; H, 5.61; N, 3.32.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Research Foundation of State University of New York; US2008/26027; (2008); A1;,
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Reference of 588-63-6, 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. 588-63-6 name is (3-Bromopropoxy)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.

General procedure: A solution of alkyl bromide (1 equiv) and sodium azide (2.5 equiv) in DMF (0.14 M) was stirred under argon at 80 °C for 18 h. After cooling at room temperature, the reaction mixture was diluted in Et2O and washed with water (×6). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give the corresponding pure azide without need of any further purification.

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

Reference:
Article; Maury, Julien; Feray, Laurence; Bertrand, Michele P.; Kapat, Ajoy; Renaud, Philippe; Tetrahedron; vol. 68; 47; (2012); p. 9606 – 9611,6;,
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Reference of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

General procedure: NaN3 (0.42 g, 6.5 mmol) was added to a stirred solution of 1-bromo-4-(3-bromopropoxy)benzene (1.47 g, 5 mmol) in DMSO (25 mL). The mixture was stirred for 12 h at room temperature, diluted with H2O (50 mL), and extracted by EtOAc (50 mL .x. 3). The organic layer was separated, dried with Na2SO4, and concentrated under reduced pressure. The residue was white solid and reacted to the next step without further purification. The synthetic method for the compound 5b was similar to the synthesis of compound 5a.

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)benzene, its application will become more common.

Reference:
Article; Wang, Shengzheng; Jin, Gang; Wang, Wenya; Zhu, Lingjian; Zhang, Yongqiang; Dong, Guoqiang; Liu, Yang; Zhuang, Chunlin; Miao, Zhenyuan; Yao, Jianzhong; Zhang, Wannian; Sheng, Chunquan; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 292 – 299;,
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Related Products of 588-63-6, 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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Scheme IV, Step S: Synthesis of 1-(3-phenoxy-propyl)-piperidine (Scheme IV, Compound 4) Mix 3-phenoxypropyl bromide (801.5 g, 3.73 mol), potassium iodide (61.8 g, 0.37 mol, 0.10 equivalents) and water (4.0 L) in a 12-L, 3-necked flask fitted with: a stirrer, thermometer in a side-arm adapter, connected to a Firestone.(R). valve and an addition funnel fitted with a gas outlet adapter, connected to a bubbler. Add piperidine (634.6 g, 7.45 mol, 2.0 equivalents) over 1 hour, without cooling under nitrogen. The temperature at the end of the addition is 40°C. Heat the reaction mixture and maintain the temperature at 50°C for 6 hours. Monitor the progress of the reaction by HPLC (Column=300 x 3.9 mm Phenomenex Bondclone 10 CN; mobile phase=65percent acetonitrile:35percent 0.1N ammonium formate buffer; flow=1.5 mUminute; wavelength=215 nm; RT: 3-phenoxypropyl bromide=2.3 minutes; 37=4.4 minutes). Typically, the conversion is 94percent. Cool the reaction mixture to ambient temperature over a time period of 14 hours and extract with dichloromethane (2 x 4.0 L). Combine the organic extracts and dry over MgSO4 (400 g). Filter off the drying agent and wash with dichloromethane (1.0 L). Concentrate the filtrate (35-40 °C/50 torr) to give 800 g, 98percent Yield) of 4, as an oil. HPLC analysis shows that 37 is 90percent pure. Purify 4 (16.5 g portion) by distillation under vacuum and collect the title compound (10 g) as a colorless liquid at 99-105°C/0.3 mm: 1H NMR (CDCl3, 200MHz) delta 1.38-1.5 (m, 2H), 1.5-1.64 (m, 4H), 1.9-2.1 (m, 6H), 4.0 (t, 2H), 6.85-6.95 (m. 3H), 7.22-7.3 (t, 2H). Analysis calculated for C14H21NO: C, 76.67; H, 9.65; 6.39. Found: C, 76.55; H, 9.50; N, 6.22. [M+H]+=220 m/e.

The chemical industry reduces the impact on the environment during synthesis (3-Bromopropoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aventis Pharmaceuticals Inc.; EP1216244; (2003); B1;,
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