Tag: M.W=200-300

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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., name: (4-Bromo-2-fluorophenyl)methanamine

Step 1: (4-Bromo-2-fluorophenyl)methanamine (924 mg, 4.53 mmol) was dissolved in pyridine and ethane sulfonyl chloride (0.82 mL, 8.60 mmol) was added to the solution at 0 C. The mixture was stirred for 1 h at 0 C. Then, the mixture was quenched with 1N HCl and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate and purified by column chromatography gave N-(4-bromo-2-fluorobenzyl)-ethanesulfonamide in pure form (1.06 g, 79%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; Bahrenberg, Gregor; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/79320; (2013); A1;,
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Reference of 13633-25-5, These common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, 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: A solution of ethyl-2-(diethoxyphosphoryl) acetate 5 in DMF(25 mL/mol) was stirred at 0 C. The base was added and the solutionwas continued to stir for 20 min before the alkyl halide wasadded drop wise. The reaction mixture was allowed to warm toroom temperature and then heated at 60 C for 18 h. After coolingthe reaction mixture was acidified with 10% citric acid andextracted with diethyl ether (3 x 30 mL). The combined organicphases were washed with H2O (3 x 30 mL), brine (1 30 mL) anddried over Na2SO4. The product 6a-c was purified with columnchromatography using 2:1 diethyl ether/pentane as eluent.

Statistics shows that 1-Bromo-4-phenylbutane is playing an increasingly important role. we look forward to future research findings about 13633-25-5.

Reference:
Article; Skagseth, Susann; Akhter, Sundus; Paulsen, Marianne H.; Muhammad, Zeeshan; Lauksund, Silje; Samuelsen, Ørjan; Leiros, Hanna-Kirsti S.; Bayer, Annette; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 159 – 173;,
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Related Products of 18392-81-9,Some common heterocyclic compound, 18392-81-9, name is 5,6-Dibromobenzo[c][1,2,5]thiadiazole, molecular formula is C6H2Br2N2S, 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 mixture of N,N?-1,3-bis(2,6-diisopropylphenyl)imidazolium chloride [51] (0.45 g, 1.06 mmol) and Pd(OAc)2 (0.13 g, 0.59 mmol) in toluene (4mL), a suspension of NaOt-Bu (0.16g, 1.66mmol) in dry toluene (3mL) was added under inert conditions. The solution was heated at 88C for 30min. This mixture was cooled to room temperature and added to a pressure tube containing 2 [41] (2.00g, 6.8mmol) in toluene (70mL). To this mixture, tert-butylamine (1.5mL, 14.27mmol) was added followed by NaO-tBu (1.60g, 16.65mmol). The pressure tube was sealed and heated for 16hat 130C. After cooling, the reaction mixture was filtered through Celite. The filtrate was collected and evaporated to yield 3 as a light brown solid (1.941g, crude yield). The crude product was engaged in the following reaction with no further purification. 1H NMR (CDCl3, 300MHz): delta 7.14 (s, 2H, ArH), 3.40 (br, 2H, NH), 1.41 (s, 18H, CH3).

The synthetic route of 18392-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tapu, Daniela; Buckner, Ossie J.; Boudreaux, Chance M.; Norvell, Bradley; Vasiliu, Monica; Dixon, David A.; McMillen, Colin D.; Journal of Organometallic Chemistry; vol. 823; (2016); p. 40 – 49;,
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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. 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5-(trifluoromethyl)aniline

Reference Example 94 Synthesis of 2-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid A mixture of 3-amino-4-bromobenzotrifluoride (1.2 g), levulinic acid (1.0 g), p-TsOH (0.1 g) and benzene (10 ml) was heated to reflux for 3 hours using a Dean Stark tube. The reaction mixture was concentrated under reduced pressure, and a mixture of palladium acetate (60 mg), tris(o-tolyl)phosphine (0.15 g), triethylamine (0.8 g) and DMF (2 ml) was stirred with the obtained residue in a sealed tube for 20 hours at 120 C. Water and ethyl acetate were added to the reaction mixture, the insoluble portion was filtered out with celite and extraction was performed with ethyl acetate, and then after combining the organic layer and drying over sodium sulfate, the product was concentrated under reduced pressure. Methanol (20 ml) and concentrated sulfuric acid (1 ml) were added to the obtained residue and the mixture was heated to reflux for 2 hours. Water was added to the reaction mixture, which was then extracted with dichloromethane, dried over sodium sulfate and concentrated under reduced pressure. 2-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester was purified from the obtained residue by silica gel column chromatography using a mixed solvent of hexane and dichloromethane. A 2 N sodium hydroxide aqueous solution (1 ml) and methanol (1 ml) were added to the obtained 2-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester, and the mixture was heated to reflux for one hour. Water was added to the reaction mixture, which was then rendered acidic with concentrated aqueous hydrochloric acid, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure, to obtain 79 mg of the title compound as a colorless powder (6% yield). The NMR data for the obtained compound were as follows. NMR: (300 MHz, DMSO-d6) delta: 2.38 (3H,s), 3.62 (2H,s), 7.23 (1H,dd), 7.5-7.7 (2H,m), 11.32 (1H,s), 12.0-12.4 (1H,m)

The synthetic route of 454-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujiwara, Shinya; Ozaki, Tomokazu; Kozono, Toshiro; Hattori, Kunihiro; Esaki, Toru; US2003/162724; (2003); A1;,
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Some common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, molecular formula is C4H3BrF4, 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: 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were added iodobenzene (3a, 0.40 mL, 3.6 mmol) and Cu2O (0.027 g, 0.18 mmol), and a DMF solution of 2-Zn (0.60 M, 1.0 mL, 0.6 mmol). The whole was heated up at 100 C and stirred at that temperature for 24 h. After cooling to room temperature, the resultant was filtered through a short pad of silica gel using hexane as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography using hexanes as an eluent, leading to the corresponding compound 4a (0.036 g, 0.17 mmol) in 29% isolated yield as a colorless oil. 3,3,4,4-Tetrafluoro-4-phenylbut-1-ene (4a) [S1] Known compound; Yield: 29% (0.036 g, 0.17 mmol); Colorless oil (hexanes, Rf = 0.57); 1H NMR (CDCl3): 5.69 (d, J = 11.6 Hz, 1H, trans-CH2CHCF2), 5.83 (dt, J = 17.2, 1.6 Hz, 1H, cisCH2CHCF2), 6.02 (ddt, J = 17.2, 11.6, 11.5 Hz, 1H, CF2CH), 7.44-7.58 (m, 5H, ArH); 13C NMR (CDCl3): 115.1 (tt, J = 248.8, 37.2 Hz, CF2), 116.4 (tt, J = 252.1, 35.5 Hz, CF2), 124.1 (t, J = 9.9Hz, CH2), 126.7 (t, J = 24.8 Hz, CF2CH), 126.9 (td, J = 6.6, 1.7 Hz, Ar), 127.0-127.7 (m, Ar), 128.2 (Ar), 131.0 (t, J = 1.7 Hz, Ar); 19F NMR (CDCl3): 112.56 (s, 2F, CF2Ar), 114.95 (d, J = 11.46 Hz, 2F, CF2CH); IR (neat): 3071, 1653, 1424, 1286, 1243, 1130, 1070, 949 cm-1 ; HRMS (FAB) calcd for [M]+ C10H8F4: 204.0562, found 204.0558.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18599-22-9, its application will become more common.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
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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. 113170-72-2, name is 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 113170-72-2

Example 21 0.2 mol of 3-bromo-5-trifluoromethyl-phenylene-diamine and 150 ml of trifluoroacetic acid were refluxed for 3 hours. For working up, excess trifluoroacetic acid was distilled off and the residue was partitioned between 100 ml of water and 300 ml of ethyl acetate. The organic phase was separated off, washed in succession with in each case 100 ml of aqueous sodium hydrogencarbonate solution and water, dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1). This gave 4-bromo-6-trifluoromethyl-2-trifluoromethyl-1H-benzimidazole of melting point 149-151 C.

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 113170-72-2.

Reference:
Patent; Bayer Aktiengesellschaft; US5656649; (1997); A;,
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Reference of 112734-22-2,Some common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, molecular formula is C7H7BrFN, 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.

N-[(4-Bromo-2-fluorophenyl)methyl]-4-tert-butylbenzamide In a 25-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, (4-bromo-2-fluorophenyl)methanamine (1.000 g, 4.90 mmol, 1.00 equiv) was dissolved in dichloromethane (20 mL), to which were added 4-tert-butylbenzoic acid (1.310 g, 7.35 mmol, 1.50 equiv), HOBT (993 mg, 7.35 mmol, 1.50 equiv), EDCI (1.409 g, 7.35 mmol, 1.50 equiv) and DIEA (1.267 g, 9.80 mmol, 2.00 equiv) in sequence at room temperature. The resulting solution was stirred for 16 h at room temperature. When the reaction was done, it was quenched by the addition of 10 mL water and the mixture was extracted with ethyl acetate (3*20 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (5% to 30% gradient) to afford N-[(4-bromo-2-fluorophenyl)methyl]-4-tert-butylbenzamide (700 mg, 39%) as yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Bromo-2-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
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Electric Literature of 445-02-3, 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. 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

Step A: N-(4-Bromo-2-trifluoromethyl-phenyl)-3,3-dimethylbutanamide 3,3-Dimethylbutanoyl chloride (617 mg, 0.64 mL, 4.6 mmol) was added to a solution of 4-Bromo-2-trifluoromethyl-phenylamine (1.0 g, 4.16 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature overnight. Water was added to the mixture and the precipitate formed collected to give the title compound as a powder (1.1 g, 79% yield).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-(trifluoromethyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Valeant Pharmaceuticals North America; US2008/139610; (2008); A1;,
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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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Bromo-3,4,5-trifluorobenzene

2L three-necked flask, nitrogen protection, cast diisopropylamine, tetrahydrofuran 750g,Cooling -40 dropping n-butyl lithium, dropping temperature insulation reaction 30min, cooling to -78 , dropping raw materials3,4,5, -trifluorobromobenzene, dropping off,-78 insulation 2h.The temperature was raised to -60 C began dropping dimethyl sulfate,Maintain the temperature is not higher than -30 , the dropping was completed naturally rose to room temperature, incubated for 30min.Stop the reaction, the pump off the pressure of tetrahydrofuran,Add 400g of water,Dichloroethane extraction, the organic phase was washed again, concentrated under reduced pressure distillation, to obtain the final product 2-methyl-3,4,5-trifluorobromobenzene purity of 99.5% or more, a yield of 61%.

According to the analysis of related databases, 138526-69-9, 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; Zhang Hao; Zhao Shimin; Xu Jianxiao; (4 pag.)CN105967974; (2016); A;,
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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. 113170-72-2, name is 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine, A new synthetic method of this compound is introduced below., Quality Control of 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine

Example 18 Preparation of 5-Bromo-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione The title compound was prepared using an adaptation of the method of Cheeseman, G. W. H., J. Chem. Soc. 1171 (1962). A mixture of diethyl oxalate (1.15 g, 7.91 mmol) and 1,2-diamino-3-bromo-5-trifluoromethylbenzene (200 mg, 0.95 mmol) was heated to reflux under N2 for 2 h. The reaction was allowed to cool to room temperature and the solid collected by vacuum filtration and rinsed with EtOH (15 mL). This white solid was dried in a drying pistol (0.05 torr, 78 C.) to yield 148.3 mg (60.7%). mp 301-304 (dec). 1 H NMR (d6 -DMSO) delta7.28 (s, 1H, ArH), 7.56 (s, 1H, ArH), 11.7 (br s, 2H, NH). 19 F NMR (C6 F6 external standard, delta-162.9) delta-57.97 (s). EIHRMS calc. for C9 H4 BrF3 N2 O2 307.9408, found 307.9411.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; The State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University; The University of Oregon; The Regents of the University of California; US5514680; (1996); A;,
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