Tag: M.W=200-300

These common heterocyclic compound, 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, 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. Product Details of 175278-09-8

4-Bromo-2-trifluoromethoxy-phenylamine (13 g, 0.05 mol) and But-2-ynedioic acid diethyl ester (10.3 g, 0.12 mol) were dissolved in EtOH (120ml) in a 500 ml round bottom flask and refluxed. The reaction was monitored by LC-MS. 3 h later; 0.3 eq. but-2-ynedioic acid diethyl ester was added. At t = 5h, the reaction mixture was concentrated down to remove the solvent under vacuum, a thick oil was obtained and was used without purification for the next step. MS [M+H]+ = 426.

The synthetic route of 4-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong, R.; DU, Zhimin; JI, Mingzhe; JIN, Haolun; KIM, Choung, U.; MISH, Michael, R.; PHILLIPS, Barton, W.; PYUN, Hyung-jung; SHENG, Xiaoning, C.; WU, Qiaoyin; ZONTE, Catalin, Sebastian; WO2011/156610; (2011); A2;,
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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 5414-19-7 as follows. Product Details of 5414-19-7

Part F:; To a DMF (9 mL) solution of Part E (1.08 g, 2.71 mmol) was added K2CO3 (1.12 g, 8.16 mmol), 18-crown-6 (0.21 g, 0.80 mmol), and bis (2-bromoethyl) ether (0.37 mL, 2.9 mmol). The slurry was stirred at 60C for 72 hr. Additional bis (2-bromoethyl) ether was added at 24 hr (0.4 mmol) and 48 hr (1.2 mmol). The solvent was stripped in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was separated, dried over MgS04, and evaporated to an oil. Recrystallization from diethyl ether produced 0. 88 g (69 %) of the desired compound in the form of a white solid. LCMS: itvz = 469.2 (M+H).

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/42521; (2005); A2;,
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Related Products 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 ¡ãC 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 ¡ãC, 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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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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-4-methoxynaphthalene

2-(4-Methoxy-1-naphthyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (S2). 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (1.92 mL, 15.00 mmol) was added dropwise to a solution of 1-bromo-4-methoxynaphthalene S1 (1.19 g, 5.00 mmol), NEt3 (2.79 mL, 20 mmol) and Pd(ddpf)Cl2.CH2Cl2 (510 mg, 0.625 mmol) in anhydrous dioxane (15 mL) and the reaction mixture heated at 100 C. for 23 h. After cooling to room temperature, the reaction was quenched cautiously with water (20 mL) and extracted with CH2Cl2 (3¡Á35 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2; EtOAc/heptane; 0-30%) afforded the pinacol ester as an off-white solid (1.09 g, 77%). 1H NMR (400 MHz, CDCl3) delta=1.41 (s, 12H), 4.02 (s, 3H), 6.82 (d, J=7.8 Hz, 1H), 7.43-7.48 (m, 1H), 7.53-7.57 (m, 1H), 8.04 (d, J=7.8 Hz, 1H), 8.28 (dd, J=0.9, 8.3 Hz, 1H), 8.75 (d, J=8.3 Hz, 1H). 13C NMR (100 MHz, CDCl3) delta=25.1, 55.6, 83.5, 103.3, 122.1, 125.0, 125.5, 127.0, 128.3, 137.0, 138.3, 158.3. HRMS (ESI+) (m/z): [M+H]+ calcd. for C17H22BO3, 285.1657; found, 285.1643.

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 5467-58-3.

Reference:
Patent; Hadjifrangiskou, Maria; Almqvist, Fredrik; Shaffer, Carrie L.; Good, James; (66 pag.)US2017/233409; (2017); A1;,
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Electric Literature of 583-19-7,Some common heterocyclic compound, 583-19-7, name is 1-Bromo-2-ethoxybenzene, molecular formula is C8H9BrO, 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 V.1 (X1 = Br, X2 = Cl): 1-bromo-2-ethoxybenzene-1-sulfonyl chloride; To a solution of 9 g (45 mmol) of 1-bromo-2-ethoxybenzene (intermediate VI.1) in 220 mL of dichloromethane, a solution of 9 mL (135 mmol) of chlorosulfonic acid in 16 mL of dichloromethane was added for one hour at -5C. Then it was stirred for an additional 1 hour, at room temperature. The reaction mixture was carefully poured over about 500 g of crushed ice and the resulting phases were allowed to decant and were separated. The organic phase was washed, successively, with 220 mL of a 5% Na2CO3 aqueous solution, 220 mL of NaHCO3 saturated aqueous solution, 220 mL of water and 220 mL of brine. Then, it was dried over anhydrous sodium sulfate and evaporated to dryness to obtain 11.91 g (89% yield) of 1-bromo-2-ethoxybenzene-1-sulfonyl chloride as a yellow oil. 1H NMR (CDCl3, 200 MHz) delta (ppm): 8.21 (d, J = 2.2 Hz, 1H); 7.96 (dd, J = 2.2 Hz, J = 9.2 Hz, 1H) ; 7.01 (d, J = 9.2 Hz, 1H); 4.24 (q, J = 7.0 Hz, 2H) ; 1.55 (t, J = 7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-ethoxybenzene, its application will become more common.

Reference:
Patent; Galenicum Health, S.l.; EP2168967; (2010); A1;,
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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 53087-13-1 as follows. HPLC of Formula: C13H11BrO

1.85 g of magnesium was suspended in 15 ML of diethyl ether, to which a catalytic amount of iodine was added and then a solution of 20.00 g of 1-(benzyloxy)-3-bromobenzene in 40 ML of diethyl ether was added dropwise and this mixture was stirred for 8 hours while heating it under reflux.. The reaction mixture was cooled to 5C, to which a solution of 6.72 ML of cyclopentanone in 20 ML of diethyl ether was added dropwise, and this mixture was stirred for one hour at room temperature.. Then an aqueous solution of ammonia chloride was added to the ice-cooled reaction mixture, and the organic phase was separated therefrom.. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure.. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to yield 7.65 g of 1-[3-(benzyloxy)phenyl] cyclopentanol as yellow oil. NMR(400MHz,CDCl3) delta value: 1.52(1H,s), 1.79-1.88(2H,m), 1.93-2.04(6H,m), 5.08(2H,s), 6.85(1H,ddd,J=8.4,2.8,1.2Hz), 7.08(1H,ddd,J=7.6,1.6,0.8Hz), 7.16-7.17(1H,m), 7.24-7.46(6H,m)

According to the analysis of related databases, 53087-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; Hirono, Shuichi; Shiozawa, Shunichi; EP1445249; (2004); A1;,
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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 101-55-3 as follows. HPLC of Formula: C12H9BrO

(1) Grignard reagent: first in a 1000mL three-necked flask, Add 600mLTHF and 200g 4 – Bromodiphenyl ether stirred solution, spare. Then in a 2000mL three-necked flask was added 21.5g of magnesium, 20 mL THF, one small Iodine, 20mL of prepared 4-bromo-diphenyl ether in THF was added dropwise, and after the initiation of heating, the remaining 4-bromo-diphenyl ether in THF was added dropwise at 30-35 C. After the addition, the mixture was incubated at 30-35 C Stirred for 1 hour, The flask was cooled to -30 C with liquid nitrogen until ready for use. (2) Borated: In the above format liquid, 100.1 g of trimethyl borate 600 mL THF solution was slowly added dropwise, Dropping process to maintain -40 ~ -30 the following, After dropping the mixture was allowed to warm to room temperature, 400 ml of 10% hydrochloric acid was added dropwise and refluxed for 1 hour. After distilling off the THF, 500 ml of cold water was added and the mixture was stirred for 30 minutes, cooled, crystallized and separated, 154.1 g of 4-phenoxybenzeneboronic acid were obtained, The yield is 90%. (3) Purification: In a 1 L three-necked flask were added 154.1 g of wet crude 4-phenoxybenzeneboronic acid, Add 200 mL of toluene to dissolve, desolvate, cool, crystallize and centrifuge to obtain 137 g of 4-phenoxybenzeneboronic acid product in a yield of 80%

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bengbu Zhong Shi Chemical Co., Ltd.; Yang Qing; Liu Hongqiang; Zhao Shimin; Xu Jianxiao; (5 pag.)CN105820184; (2016); A;,
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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 59557-91-4 as follows. name: 4-Bromo-2-methoxyaniline

Step 1: To a solution of 4-bromo-2-methoxyaniline (2.0 g, 9.9 mmol) in MeCN (50 mL) was added para-toluenesulfonic acid (5.1 g, 27 mmol). The resulting mixture was cooled in an ice water bath. A solution of NaNO2 (1.36 g, 19.7 mmol) and KI (4.11 g, 24.8 mmol) in water (50 mL) was then added, and the resulting mixture was stirred for 5 min. The mixture was then removed from the ice water bath. Once consumption of starting material was observed, the reaction mixture was partitioned between water and EtOAc. The organic phase was concentrated and the resulting crude residue was purified by silica gel chromatography to afford 4-bromo-1-iodo-2-methoxybenzene

According to the analysis of related databases, 59557-91-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5, SDS of cas: 588-96-5

Preparation Example 6 Synthesis of 1-(benzyloxy)-2-bromo-4-(4-ethoxybenzyl)benzene; Benzyl bromide (3.1 mL, 0.026 mol) was added to a mixture of 3-bromo-4-hydroxybenzaldehyde (5.0 g, 0.025 mol), tetrabutylammonium iodide (0.92 g, 2.5 mmol), potassium carbonate (6.9 g, 0.050 mol) and N,N-dimethylformamide (70 mL) at room temperature and stirred for 2.5 hours. An ice-water mixture (100 mL) was poured to the reaction mixture and the resultant solution was stirred for one hour. A resulting precipitate was filtered and dried to obtain 4-benzyloxy-3-bromobenzaldehyde (7.1 g, 98%) as a pale yellow powder. Then, 1.6 M n-butyllithium hexane solution (22.9 mL) was added to a mixture of 4-bromophenetole (7.3 g, 0.037 mol) and tetrahydrofuran (70 mL) at -78C. After stirred for 0.5 hours, 4-benzyloxy-3-bromobenzaldehyde (7.0 g, 0.024 mol) in a tetrahydrofuran (70 mL) solution was added and further stirred for 15 minutes, and the reaction mixture was warmed to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain colorless oily [4-(benzyloxy)-3-bromophenyl](4-ethoxyphenyl)methanol (8.7 g, 86%). Then, Et3SiH (6.7 mL, 0.042 mol) and BF3¡¤Et2O (2.7 mL, 0.021 mol) were added sequentially to a chloroform (90 mL) solution of [4-(benzyloxy)-3-bromophenyl](4-ethoxyphenyl)methanol (8.7 g, 0.021 mol) at -15C. After stirred for one hour, the reaction mixture was warmed to room temperature. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain a colorless oily title compound (8.8 g, quant). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.40 (t, J=7.0 Hz, 3 H) 3.82 (s, 2 H) 4.00 (q, J=7.0 Hz, 2 H) 5.12 (s, 2 H) 6.78 – 6.87 (m, 3 H) 6.98 – 7.10 (m, 3 H) 7.27 – 7.50 (m, 6 H).

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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1845095; (2007); A1;,
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Related Products of 35896-58-3, These common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, 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 mixture of 2,3,4,5-tetramethoxytoluene (2.12 g, 10 mmol) and 1,1-dichlorodimethyl ether (1.8 mL, 20 mmol) in DCM (200 mL) was stirred at room temperature (rt), then the solution was allowed to cool to 0 oC and was added titanium tetrachloride (2.18 mL, 20 mmol). The mixture was allowed to warm to rt and stirred for 4 hours. The ice water was added slowly to quench the reaction and extracted with DCM, washed with brine and dried over Na2SO4, filtered and evaporated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (EtOAc / petroleum ether = 1 / 20) to yield the target products (2 g, 83%) as colorless oil. 1H NMR (400 MHz, CDCl3) delta 10.43 (s, 1H), 4.02 (s, 3H), 3.94 (s, 3H), 3.91 (s, 3H), 3.76 (s, 3H), 2.46 (s, 3H). MS (ESI): m/z 241.1 [M+H]+.

The synthetic route of 35896-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Yuyang; Tang, Fei; Xue, Xiaoqian; Luo, Jinfeng; Hussain, Muzammal; Huang, Yanhui; Wang, Zhen; Jiang, Hao; Tu, Zhengchao; Zhang, Jiancun; Bioorganic Chemistry; vol. 89; (2019);,
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