Tag: M.W=200-300

450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, 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 total of 1.64 ml of diisopropylamine was dissolved in 27 ml of tetrahydrofuran, 6.8 ml of a 1.57 M solution of n-butyllithium in hexane was added at -50C under stirring, and the mixture was stirred at -30C for 30 minutes. After cooling to -60C, 2 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a was added and the mixture was stirred at -60C for 1 hour. Then, 1.55 ml of 3-fluoro-benzaldehyde was added, followed by stirring for 1 hour. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated, to give 2.4 g of the title compound as a yellow-brown oil.1H-NMR ( 400 MHz, CDCl3 ) d 3.52 ( 3H, s ), 3.56 ( 1H, d, J = 10.4 Hz ), 6.16 ( 1H, d, J=11.6Hz ), 6.86 ( 1H, t, J = 8.8 Hz ), 6.92 – 6.99 ( 1H, m ), 7.07 – 7.16 ( 2H, m ), 7.30 ( 1H, td, J = 8.0, 6.0 Hz ), 7.51 ( 1H, dd, J = 8.8, 6.0 Hz )

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 450-88-4.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
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104197-14-0, Adding some certain compound to certain chemical reactions, such as: 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, 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 104197-14-0.

A mixture of 4-bromo-2,6-difluorophenyl methyl ether (5.Og), 1 ,1-dimethylethyl 1- piperazinecarboxylate (5.Og), 2-biphenylyl[bis(1 ,1-dimethylethyl)]phosphane (0.666g), palladium acetate (0.246g), sodium tert-butoxide (3.01 g) in toluene(30ml) was heated at 9O0C for 16 hours. After cooling ,The reaction mixture was diluted with diethyl ether, filtered through a pad of celite. Then concentrated in vacuo to give a black oil. The desired product was isolated by column chromatography on silica eluting with a gradient of 5 to 100% ethyl acetate in pentane. The title compound was obtained as a solid, (90% yield), LC/MS (ESI) Found 229 (M-BOC+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 104197-14-0.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/94842; (2006); A1;,
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A common heterocyclic compound, 583-19-7, name is 1-Bromo-2-ethoxybenzene, molecular formula is C8H9BrO, 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. 583-19-7.

Reference Example 160 In THF (120 ml) was dissolved 1-bromo-2-ethoxybenzene (12.0 g). To the mixture was added dropwise at -78 C. 1.6M n-butyllithium/hexane (41.1 ml), and the mixture was stirred for 1 hour. To the mixture was added dropwise a solution of trimethylborate (12.4 g) in THF (12.4 ml), and the mixture was stirred for 30 minutes and warmed to room temperature. To the mixture was added 2N hydrochloric acid (48 ml), and the mixture was stirred for 15 minutes. The reaction mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was washed with hexane/isopropylether to give 2-ethoxyphenyl borate (7.1 g). 1H-NMR (200 MHz, DMSO-d6) delta 1.37 (3H, t, J=7.0 Hz), 4.09 (2H, q, J=7.0 Hz), 6.89-6.99 (1H, m), 7.33-7.42 (1H, dd, J=7.2, 1.6 Hz), 7.66 (2H, s).

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6235771; (2001); B1;,
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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;,
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Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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. 5905-69-1

Piperidine-4-carboxylic acid ethyl (3.52mL, 22.9mmol), and 1-Bromo-4- (difluoromethoxy) benzene (4.25g, 19.1mmol) of TorrEne (122 mL) to the solution, sodium tert- butoxide (2.29g, 23.8mmol), palladium acetate (II) (428mg, 1.91mmol), and, tri -tert- butyl phosphine (370muL, 1.52mmol) was added, and 30 minutes at 80 And the mixture was stirred. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the resulting organic layer was washed with saturated brineAfter, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Siri resulting residue wasGel column chromatography [elution solvent: hexane / ethyl acetate = 100 / 0-90Purification by / 10], the title compound (3.17 g, yield: 56%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5905-69-1, its application will become more common.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); A;,
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19056-40-7, These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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.

Under an atmosphere of nitrogen, in a 100 mL round-bottomed flask at 0¡ã C., 4-bromo-3-methoxyaniline (2 g, 9.9 mmol) and KOH (6.93 ml, 13.9 mmol) were combined with dichloromethane (30 ml) to give a light brown solution. Then 4-bromobutanoyl chloride (1.84 g, 1.15 ml, 9.9 mmol) was added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into 50 ml dichloromethane and extracted with water (3*20 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in 30 ml dichloromethane. Then tetrabutylammonium bromide (63.8 mg, 198 mumol) and KOH (50percent, 6 ml) were added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into dichloromethane (50 ml) and extracted with water (3*20 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 50percent EtOAc in heptane). The title compound was obtained as a off-white crystalline (1.92 g, 71.8percent). MS (m/e)=272.1 [M+H]+.

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 19056-40-7.

Reference:
Patent; Hoffmann-La Roche Inc.; Jakob-Roetne, Roland; Wichmann, Juergen; Peters, Jens-Uwe; Jagasia, Ravi; (33 pag.)US2016/326150; (2016); A1;,
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5111-65-9,Some common heterocyclic compound, 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, molecular formula is C11H9BrO, 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 21.2: 6-methoxy-naphthalen-2-ylamine A solution of 2-bromo-6-methoxy-naphthalene (237 mg, 1 mmol), Pd (dba)2 mg, 0.05 mmol), tri-t-buthylphosphonium tetrafluoroborate (14 mg, 0.05 mmol), and lithium bis (trimethylsilyl)amide (1 M in hexane, 1.1 mL, 1.1 mmol) is stirred in toluene (2.5 mL) under argon for 6 h. The reaction mixture is taken in diethyl ether (20 mL), and quenched with 1 M HCI. The organic phase is extracted with water, the combined aqueous phases are treated with 1 M sodium hydroxide and extracted with DCM. The combined organic phases are dried over magnesium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (ethyl acetate) to afford 6-methoxy- naphthalen-2-ylamine (110 mg, 64 %), HPLC tR : 3.07, (M+H) + = 173.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-6-methoxynaphthalene, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
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35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, 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. 35896-58-3

2,3,4,5-Tetramethoxytoluene 3 (2.1 g, 10 mmol) and NaBr (1.1 g, 10 mmol) were dissolved in AcOH (5 mL), a solution of 30% H2O2 (1.2 mL, 10 mmol) was added dropwise over 5 min at room temperature. The mixture was stirred and heated at 40 C for 1 h and quenched with H2O( 5 mL) and extracted with diethyl ether (3 ¡Á 30 mL). The combined organic phases were washed with saturated NaHCO3(3 ¡Á 10 mL) until pH 7, then dried over anhydrous Na2SO4,and evaporated under reduced pressure to give yellow oil 4 (2.9 g) in quantatitive yield. 1H NMR (400 MHz, CDCl3) delta 3.92 (s, 3H, OCH3), 3.91(s, 3H, OCH3), 3.85 (s, 3H, OCH3), 3.79 (s, 3H, OCH3),2.30 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)delta 148.3, 147.2, 146.3,145.5, 127.3, 114.3, 61.4 (OCH3), 61.1 (OCH3), 60.9(OCH3), 60.8 (OCH3), 15.9 (CH3). GC-MS (EI): m/z = 290.

Statistics shows that 35896-58-3 is playing an increasingly important role. we look forward to future research findings about 1,2,3,4-Tetramethoxy-5-methylbenzene.

Reference:
Article; Qiu, Yong-Fu; Lu, Bin; Yan, Yi-Yu; Luo, Wan-Yue; Wang, Jin; Hu, Xiao; Chemical Papers; vol. 73; 11; (2019); p. 2745 – 2748;,
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A common heterocyclic compound, 43229-65-8, name is N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, molecular formula is C17H21NO, 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. 43229-65-8.

Synthesis of 4-benzyloxy-3-methoxymethyl-alpha[N-benzyl-N(alpha-methyl-4-methoxyphenethyl)amino]acetophenone Amounts of 39.5 g of the compound obtained in the step C1 and 57.7 g of N-benzyl-N(alpha-methyl-4-methoxyphenethyl)amine are stirred for 6 hours in 200 ml of acetonitrile. The crystals precipitated are filtered off, and the filtrate is concentrated, to give the object compound. The compound is used for the following step without purification.

The synthetic route of N-Benzyl-1-(4-methoxyphenyl)propan-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US4317930; (1982); A;,
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54314-84-0, name is ((3-Bromopropoxy)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. Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; WASHIO, Yoshiaki; (112 pag.)WO2019/3141; (2019); A1;,
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