Category: bromides-buliding-blocks

Electric Literature of 2695-47-8,Some common heterocyclic compound, 2695-47-8, name is 6-Bromo-1-hexene, molecular formula is C6H11Br, 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: A 70 ml oven dried autoclave containing a stirrer bar wascharged the AgI (0.5 mg, 0.002 mmol) and Cs2CO3 (978 mg, 3.0mmol). The autoclave was purged three time with CO2 and theterminal alkynes 1 (2.0 mmol), bromides 2 (3.0 mmol), and dryDMF (20 ml) were then added sequentially via a syringe. Theautoclave was then sealed and pressurized to the appropriatepressure with CO2. The reaction mixture was then stirred at 60C for 24 h and the autoclave was cooled to room temperatureand the remaining CO2 slowly vented from the system. Thereaction mixture was diluted with water (30 ml) and extractedwith ethyl acetate (30 ml × 3). The combined organic layerswere washed with water and brine, dried over Na2SO4, andfiltered. The solvent was removed under vacuum. The productwas isolated by column chromatography on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-1-hexene, its application will become more common.

Reference:
Article; Zhang, Linlin; Zhang, Wenzhen; Shi, Linglong; Ren, Xiang; Lue, Xiaobing; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 6; (2013); p. 1179 – 1186;,
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Some common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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. Quality Control of 1-Bromo-3,4,5-trifluorobenzene

General procedure: To a mixture of 1,3,5-triazine(0.5 mmol), aryl halide (0.5 mmol), DMEDA (0.45 mmol)and K2CO3 (1 mmol) in MeCN (3 mmol) was added CuI (0.15mmol). The resulting mixture was stirred at reflux. After completionof the reaction, the reaction mixture was cooled to r.t.,concd NH3 (4 mL) and sat. NaCl (10 mL) were added, and theorganic phase was then extracted with EtOAc (3 × 15 mL). Theorganic phase was dried over anhyd Na2SO4. The crude residuewas obtained after evaporation of the solvent in vacuum, andthe residue was purified by flash chromatography with petroleumand EtOAc as the eluent to give the pure product. N2-(4-Methoxyphenyl)-N4,N4-dimethyl-6-phenyl-1,3,5-triazine-2,4-diamine (3a):

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 138526-69-9, its application will become more common.

Reference:
Article; Li, Jin Jing; Wu, Kong; Zhou, Wei; Wang, Hong; Cui, Dong-Mei; Zhang, Chen; Synlett; vol. 27; 13; (2016); p. 1993 – 1996;,
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Reference of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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.

Example 29 1,3-Dibromo-2-methylbenzene A solution of (3,5-dibromo-4-methylphenyl)amine dissolved in water (80 mL) and concentrated HCl (7.5 mL) stirring for 20 min, then the mixture was cooled to 0~5 C., and the solution of NaNO2 (3.4 g/30 mL H2O) was added. The reaction mixture was stirred for 2 h at 0~5 C., then the suspension was added to hypophosphorous acid solution (50%, 27.9 g), which was cooled to 0 C. The mixture was stirred at room temperature overnight. Then it was extracted with CH2Cl2 (100 mL*2) and the combined organic layers were washed with brine (30 mL) and dried over Na2SO4. After silica column chromatography, (eluted with petroleum ether), 3.57 g product was obtained, as colorless liquid. 1H NMR (400 MHz, CDCl3): delta 2.57 (s, 3H), 6.89 (t, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-4-methylaniline, its application will become more common.

Reference:
Patent; Glaxo Group Limited; US2009/197871; (2009); A1;,
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Synthetic Route of 74586-53-1, These common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, 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 3-bromo-5-methyl-aniline (1.86 g, 10 mmol), 2-chloroethanol (3.22 g, 40.00 mmol), KI (166 mg, 1.00 mmol) and CaCO3 (2.00 g, 20.00 mmol) in water (6 mL) and EtOH (6 mL) was heated at 100C for 36h, then at 120C for 20h. The reaction mixture was cooled to RT, diluted with EtOAc, washed with H20, sat. NaC1 and dried then evaporated under reduced pressure. The crude material was subjected to ISCO purification (40g silica; 0 % to 10% of MeOH in DCM) to give 2- [3-bromo-N-(2-hydroxyethyl)-5-methyl-anilino] ethanol YL4a (1.4 g, 51%). ?HNMR (300 MHz, CDC13) oe 6.71 (d, J = 22.0 Hz, 2H), 6.47 (s, 1H), 3.87 (t, J = 4.9 Hz, 4H), 3.61 – 3.53 (m, 4H), 3.41 (s, 2H), 2.29 (s, 3H) ppm. ESI-MS m/z calc. 273.04, found 274.31 (M+1)+; Retention time: 0.68 minutes.

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DAVIES, Robert, J.; CAO, Jingrong; COCKERILL, Meghan, Elise; COLLIER, Philip, Noel; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GAO, Huai; GOLDMAN, Brian, Anthony; GREY, Ronald, Lee; GRILLOT, Anne-laure; GU, Wenxin; HENDERSON, James, A.; IRARRAZAVAL, Raul Eduardo, Krauss; KOLPAK, Adrianne, Lynn; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MALTAIS, Francois; MESSERSMITH, David; PIERCE, Albert, Charles; PEROLA, Emanuele; RYU, Elizabeth Jin-Sun; SYKEN, Joshua; WANG, Jian; (706 pag.)WO2016/197009; (2016); A1;,
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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. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H11Br2N

General procedure: To the suspension of compound 11a-11e or 13 (1.5 mmol) inDCM (3 mL) was added TFA (3 mL). The mixturewas stirred at roomtemperature for 2 h and was concentrated under vacuum. Theproduct was then dissolved in DMF (6 mL) and added Et3N (1 mL)without further purification. The reaction mixture was stirred for1 h and was added CS2 (0.14 mL, 2.25 mmol) to continuously stir for 30 min. A series of different of halogen or alkene substitutedcompounds (1.5 mmol) were added respectively and the mixturewas stirred at 50 C overnight. The mixture was cooled to roomtemperature and extracted with dichloromethane (20 mL x 3). Theorganic phase was washed with brine (15mL x 3), dried overanhydrous Na2SO4 and concentrated under vacuum. The residuewas purified by column chromatography to provide the target products.

The synthetic route of 2862-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
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Synthetic Route of 10485-09-3, A common heterocyclic compound, 10485-09-3, name is 2-Bromoindene, molecular formula is C9H7Br, 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 1.45 g (63.5 mmol) piece of magnesium was charged into a sufficiently dried and argon-substituted 200 mL reactor, and stirred vigorously for 30 minutes while heating under reduced pressure. After cooling to room temperature, a reflux condenser was attached, and a piece of iodine and 15 mL of tetrahydrofuran were charged and stirred. A 10 mL diluted solution of 2.93 g (15.0 mmol) of 2-bromoindene is added dropwise (1.0 mL after addition, followed by heating to reflux until the color of iodine disappears with a dryer, remaining after dropping of the reaction drop) It stirred at room temperature after completion | finish for 2 hours.The reaction solution is diluted with 9.00 mL (75.3 mmol) of dimethylsilyl dichloride in 10 mL of n-hexane diluted solution.The reaction was slowly added at -78 C with cooling, and stirring was continued for 20 hours while returning to room temperature. After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 10 mL of tetrahydrofuran and 1.50 mL (16.0 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue.Synthesized by the method described in JP-A-201-145240 in a fully dried, argon-substituted 100 mL reactor.5.03 g (15.0 mmol) of 7- (3,5-di-tert-butyl-4-methoxyphenyl) -1-indene and 15 mL of tetrahydrofuran are charged, and 9.70 mL of n-butyllithium solution (hexane solution, 55 M (15.0 mmol) was added and stirred at room temperature for 2 hours. This solution was added dropwise to the previously diluted reaction residue diluted solution cooled to -78 C., and stirring was continued for 19 hours while slowly returning to room temperature. Saturated aqueous ammonium chloride solution was added, the solubles were extracted with n-hexane, and the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the desired product represented by the following formula (A-2L) (hereinafter referred to as compound (A-2L)) Was obtained as an isomer mixture of 5.08 g (yield 67%).

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
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Reference of 69321-60-4,Some common heterocyclic compound, 69321-60-4, name is 2,6-Dibromotoluene, molecular formula is C7H6Br2, 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 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was purged with nitrogen and charged with 2,6-dibromotoluene (2.50 g, 10.0 mmol), N-bromosuccinimide (1.78 g, 10.0 mmol) and carbon tetrachloride (40 iriL). The solution was heated to 80 C (oil bath temperature), and 2,2′-azobisisobutyronitrile (164 mg, 1.00 mmol) was added. The resulting mixture was refluxed for 14 h. After that time, the mixture was cooled to room temperature and filtered. The filter cake was washed with carbon tetrachloride (2 x 20 iriL). The filtrate was diluted with ethyl acetate (200 iriL) and washed with water (40 mL), saturated aqueous sodium bicarbonate (40 iriL) and brine (40 iriL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford a quantative yield (3.28 g) of l,3-dibromo-2-(bromomethyl)benzene as a yellow solid: mp 77-78 C; ]H NMR (300 MHz, CDC13) delta 7.55 (d, 2H, / = 8.1 Hz), 7.07 (t, IH, 7 = 8.1 Hz), 4.83 (s, 2H)

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

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
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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. 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, A new synthetic method of this compound is introduced below., Product Details of 452-63-1

2-Bromo-5-fluorotoluene (8 P. L, 0.11 MMOL) was dissolved in 1 mL dry 1, 4-dioxan in a vial under an argon atmosphere. Compound 430 (42 mg, 0.09 MMOL) was added and dissolved in the solvent. Rac-BINAP (2.1 mg, 0.003 MMOL), PD2 (dba) 3 (2.0 mg, 0.002 MMOL) and CS2CO3 (41 mg, 0.13 MMOL) were added, and the reaction mixture was stirred under an argon atmosphere at 100 C for 72 h. The reaction mixture was filtered and then dissolved in THF (1.00 mL). Tetrabutylammonium fluoride trihydrate (37 mg, 0.12 MMOL) was added to the solution and the mixture was stirred at 60 C for 45 min. The reaction mixture was poured into a mixture of EtOAc/water. The organic phase was washed with NA2CO3 (aq. ), water, dried (MgS04), filtered, and concentrated in vacuo to afford the crude product. The crude product was purified by chromatography eluting EtOAc to afford the title compound as yellow/brown oil. 13C NMR (CDCI3) 8 195.6, 167.8, 160.6, 150.4, 141.2, 140.2, 136.5, 135.7, 134.3, 133.6, 131.5, 131.4, 128.8, 127.4, 127.4, 126.9, 117. 8, 115.2, 113.9, 111.7, 77.2, 62.2, 42.9, 20.2, 18.1.

The synthetic route of 452-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
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Synthetic Route of 4101-68-2, 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. 4101-68-2, name is 1,10-Dibromodecan, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred suspension of salicyaldehyde (2 mL, 20 mmol) and potassiumcarbonate (5.52 g, 40 mmol) in DMF (100 mL) was added 1,10-dibromodecane (10.8mL, 48 mmol). The mixture was stirred at 80 C for 3 h, and the solvent was evaporated under reducedpressure. The resulting residue was triturated with ether (1000 mL), and theorganic phase was washed with dilute sodium hydroxide solution, water, brine,and dried over sodium sulfate. After evaporation of the solvent, the residuewas purified by column chromatography (petroleum/ethyl acetate, 20:1), toafford compound 2 (2.45 g, 36%) as an oil. 1H NMR(300 M,CDCl3): d 1.31-1.46 (m, 12 H), 1.82-1.87 (p, 4 H), 3.41 (t, J =6.90 Hz, 2 H), 4.07 (t, J = 6.30 Hz, 2 H), 6.99 (m, 2 H), 7.52 (m, 1 H), 7.81(m, 1 H), 10.50 (s, 1 H). MS (EI) (m/e): 340 (M-H+). Anal. Calcd forC17H25BrO2: C, 59.83%; H, 7.38%; O, 9.38%.Found: C, 59.32%; H, 7.98%.

The chemical industry reduces the impact on the environment during synthesis 1,10-Dibromodecan. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Hui; Li, Zhan-Ting; Chinese Chemical Letters; vol. 25; 5; (2014); p. 659 – 662;,
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Application of 656-64-4, These common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, 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.

EXAMPLE 195 4-[(3-Bromo-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile A mixture of 3.8 g (16.33 mmol) of 4-chloro-6-nitro-3-quinolinecarbonitrile and 3.7 g (20 mmol) of 3-bromo-4-fluoroaniline in 200 mL of ethanol was refluxed for 3hr. After the solvent was removed, the residue as dissolved in ethyl acetate and washed with sodium bicarbonate. The product was collected as a pale yellow solid, 6.5 g (71%); ESMS m/z 387.3, 389.2, mp 269-270 C. (dec).

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6002008; (1999); A;,
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