Tag: M.W=200-300

Application of 445-02-3, A common heterocyclic compound, 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

To a mixture of 2-amino-5-bromobenzotrifluoride (1.0 g, 4.17 mmol) in DCM (10 mL) at 0-5C was added NEt3 (1.16 mL, 8.33 mmol), then methanesulfonyl chloride (0.389 mL, 5 mmol) dropwise. The reaction mixture was stirred at rt for 4 days. After 2 days, more NEt3 was added (1.16 mL, 8.33 mmol). As there was no evolution after 3 days, more NEt3 (0.580 mL, 4.17 mmol) and methanesulfonyl chloride (0.324 mL, 4.17 mmol) were added. The reaction was not completed, so the reaction mixture was then heated in a microwave oven at 1 10C for 20 min. There was no evolution, so the reaction was stopped. The reaction mixture was diluted with water and DCM. Layers were separated. The organic layer was washed with water, dried over MgS04 and evaporated. Purification by Flash chromatography using CombiFlash Companion ISCO system (Redisep silica 40g column, eluting with Cyclohexane/EtOAc 100:0 to 70:30) did not give the pure compound. Purification by prep HPLC using Gilson system (SunFire C18 column, eluting with H20 + 0.1 % TFA / CH3CN 20% to 85%) gave the title compound (404 mg, 31 % yield) as a white solid. 1H-NMR (400 MHz, DMSO-de, 298 K): delta ppm 3.12 (s, 3H) 7.55 (d, 1 H) 7.91 (d, 1 H) 7.92 (s, 1 H) 9.56 (s, 1 H). MS(10): 316.3-318.2 [M-1 ]

The synthetic route of 445-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Bromide – Wikipedia,
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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. 586-77-6, name is 4-Bromo-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromo-N,N-dimethylaniline

General procedure: A round-bottom flask was chargedwith N,N-dialkyl aniline dissolved in toluene solution, under N2 condition. TBHP was added drop wise and reaction was stirred for 2 min. Triethylamine was added thereafter, and then the contents of the reaction were stirred for 3 h at 110 C under inert N2 condition. The reaction mixture was washed 2-3 times with H2O and ethyl acetate. The upper organic layer was separated and dried over sodium sulphate and then subjected to rotavapour. The crude mixture was purified by column chromatography on silica gel (60-120).

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 586-77-6.

Reference:
Article; Botla, Vinayak; Barreddi, Chiranjeevi; Daggupati, Ramana V; Malapaka, Chandrasekharam; Journal of Chemical Sciences; vol. 128; 9; (2016); p. 1469 – 1473;,
Bromide – Wikipedia,
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Related Products of 129316-09-2, A common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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 1 : 1-(3-Bromo-5-(terf-butyl)phenyl)cvclobutanol (P23a) To an oven dried 100 mL 3-neck flask was added 1 ,3-dibromo-5-(terf-butyl)benzene (500 mg, 1.72 mmol) in dry THF (30 mL) under N2 and the mixture was cooled to -78C. n-BuLi (2.5M, 1 mL) was added and the mixture was stirred at -78C for 1 h. Then cyclobutanone (181 mg, 2.58 mmol) was added. After the reaction was complete (monitored by LC-MS) the mixture was quenched with aq. NH4CI and extracted with EA. The organic layer was dried over MgS04, filtered and evaporated to give compound P23a (243 mg, 50%) as a yellow solid.

The synthetic route of 129316-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2013/79223; (2013); A1;,
Bromide – Wikipedia,
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Related Products of 2862-39-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of 6-(4-chlorophenyl)-5-(3, 8-dimethyl-[1 ,2,4]triazolo[4, 3-a]pyridin-6-yl)-3-methyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (Step 10 of Example 3, 100 mg, 0.255 mmol)in DMF (4 mL) was added NaH (13.27 mg, 0.332 mmol) under Ar. After 30 mm at rt, 3-bromo-1- methypyrrolidin-2-one (54.5 mg, 0.306 mmol) was added. The reaction mixture stirred for 1 h at rt, quenched with a saturated aqueous solution of NaHCO3 (75 mL) and extracted with EtOAc (2 x 75 mL). The organic layers were combined, washed with a saturated aqueous solution of NaHCO3 (75 mL), dried on Na2504 and evaporated. The residue was purified by silica gelchromatography on Combiflash Isco (eluent: DCM/MeOH; gradient: 0-10% MeOH in 12 mm, 2 mm 10% MeOH; flow: 18 mL/min) and subsequent SF0 to afford 12 mg of diastereomerA and 25 mg of diastereomer B. The title compound was prepared using an analogous procedure to that described in Example 126 but using dimethylaminoethyl bromide hydrobromide (71.3 mg, 0.306 mmol, 1.2 eq) and 3eq of NaH. The crude product was purified by silica gel chromatography on Combiflash Isco (eluent: DCM/MeOH; gradient: 0-10% MeOH in 12 mm, 3.6 mm 10% MeOH; flow: 18 mL/min) and subsequent trituration of the resulting material in diethyl ether to afford (65 mg) of the title compound as a colorless solid. Rt: 0.62 mm (LC-MS 1); ESI-MS mlz: 463.2 [M+H] (LC-MS 1); 1H NMR (400 MHz, DMSO-d6) O 8.31 (d, J = 1.7 Hz, 1H), 7.42- 7.26 (m, 5H), 6.71 (5, 1H), 6.42(5, 1H), 3.72-3.57 (m, 1H), 3.57-3.44 (m, 1H), 2.59 (5, 3H), 2.41 (5, 3H), 2.29-2.18 (m, 1H),2.14 (5, 3H), 2.08- 1.91 (m, 7H).

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, 2-Bromo-N,N-dimethylethanamine hydrobromide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BOLD, Guido; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUeEGER, Heinrich; VAUPEL, Andrea; WO2015/75665; (2015); A1;,
Bromide – Wikipedia,
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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. 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Computed Properties of C8H10BrN

To a solution of compound 14 (23.1 g, 115.5 mmol) in methylene chloride (500 mL) was added alpha-bromo-2?-acetonapthone (27.9 g, 110.0 mmol) and the resulting mixture was stirred at 0¡ã C. for 1 h prior to the addition of triethylamine (15.3 mL, 47.4 mmol). The reaction mixture was stirred at 0¡ã C. for 2 h. The resulting mixture was diluted with water (200 mL) and the aqueous phase was extracted with additional methylene chloride (2¡Á200 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated to afford compound 15 (44.5 g) as a light yellow oil, which was used in the next step without further purification: 1H NMR (CDCl3, 500 MHz) 8.49 (s, 1H), 8.01 (dd, J=8.8, 1.8 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.90-7.84 (m, 2H), 7.62-7.52 (m, 3H), 7.40 (d, J=8.0 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.19 (t, J=7.7 Hz, 1H), 3.91 (s, 2H), 3.68 (s, 2H), 2.40 (s, 3H)

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; Qiu, Jun; Gao, Qui; Liu, Shuang; Hu, Min; Yang, Yuh-Lin Allen; Isherwood, Matthew; Amin, Rasidul; US2014/275101; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1000994-95-5, name is 1-Bromo-4-(1,1-difluoroethyl)benzene, belongs to bromides-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. Recommanded Product: 1000994-95-5

Nitrogen,Titration in the following -60 1.6M n-butyllithium in hexane (0.4 mL)in1-Bromo-4- (1,1-difluoroethyl) benzene(0.17 g)Of tetrahydrofuran (0.61 g)The solution was stirred for an additional 1 hour and titrated for 4 minutes5-cyclopropyl-6-methoxymethylpyridinecarbonitrile(0.10 g)In tetrahydrofuran (0.30 g).After stirring for 2 hours and 2 minutes, the temperature was further raised to room temperature.After adding 5% aqueous hydrochloric acid solution (0.93 g) and stirring,Water and ethyl acetate were added,The mixture was separated into a mixture of an organic layer and an aqueous layer.Ethyl acetate (4 mL) was added to the resulting aqueous layer,Mixed and separated into an organic layer and an aqueous layer.Mixing the organic layers of both,The mixture was separated by adding 5% aqueous sodium hydrogencarbonate solution, and the organic layer and the aqueous layer were mixed.Ethyl acetate (2 mL) was added to the resulting aqueous layer,Mixed and separated into an organic layer and an aqueous layer.The organic layers were mixed, and the organic layer and the aqueous layer were mixed by adding water. Ethyl acetate (2 mL) was added to the obtained aqueous layer, mixed, and separated into an organic layer and an aqueous layer. The organic layers were mixed, dried by addition of sodium sulfate, and after the desiccant was filtered off, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane / ethyl acetate = 49/1, v / v)To obtain the title compound (0.14 g, yield 75.1%) as a pale yellow oily substance.

The synthetic route of 1000994-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; YOSHINO, HIRONOBU; UMEDA, YASUHIRO; TAKEOKA, JUN; NAGAYA, AKIHIRO; SUGAWARA, YUDAI; YOSHINO, MADOKA; (54 pag.)TW2016/5826; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 54962-75-3,Some common heterocyclic compound, 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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 mixture of CuI (190mg, 1mmol), 4-methyl-1H-imidazole (1.64g, 20mmol), Cs2CO3(3.25g, 10mmol), 3-bromo-5-(trifluoromethyl)aniline (2.40g, 10 mmol), 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone (350mg, 2mmol) and DMF (30mL) was added to a bottom, the bottom was evacuated and backfilled with argon (this procedure was repeated three times), then the mixture was heated to 130 C for 24 h under argon. After cooling to room temperature, the solvent was removed under vacuum and the residue was purified by column chromatography on silica gel to afford the crude product. The crude product was recrystallized as a white solid (1.7 g, 71%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Article; Wang, Deping; Zhang, Zhang; Lu, Xiaoyun; Feng, Yubing; Luo, Kun; Gan, Jirong; Yingxue, Liu; Wan, Junting; Li, Xiang; Zhang, Fengxiang; Tu, Zhengchao; Cai, Qian; Ren, Xiaomei; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 21; 7; (2011); p. 1965 – 1968;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1,4-Dibromo-2,3-difluorobenzene

Under a nitrogen atmosphere, 7.08 g (35.9 mmol) of 3-bromo-2-chlorothiophene (Tokyo Chemical Industry Co., Ltd.) and 70 ml of THF (dehydrated grade) were added to a 300 ml Schlenk reaction vessel. The solution was cooled to 0 C., and 18.5 ml (37.0 mmol) of a THF solution of isopropylmagnesium chloride (Sigma-Aldrich, 2.0 M) was added dropwise. The mixture was aged at 0 C. for 1 hour (preparation of Grignard reagent). Meanwhile, in a nitrogen atmosphere, 5.90 g (43.2 mmol) of zinc chloride (Wako Pure Chemical Industries, Ltd.) and 60 ml of THF (dehydration grade) were added to another 500 ml Schlenk reaction vessel and cooled to 0 C. To the obtained white fine slurry solution, the Grignard reagent of 3-bromo-2-chlorothiophene previously prepared was dropped using Teflon cannula, and further 5 ml of THF (dehydration grade) was charged into a 300 ml Schlenk reaction vessel And Teflon cannula were added while washing. The resulting mixture was stirred at 0 C. for 30 minutes and further at room temperature for 90 minutes. 3.26 g (12.0 mmol) of 1,4-dibromo-2,3-difluorobenzene (Tokyo Chemical Industry Co., Ltd.) as a white fine slurry solution of the produced 2-chlorothienyl-3-zinc derivative and tetrakis Phosphine) palladium (Tokyo Chemical Industry Co., Ltd.) (0.181 mmol, 1.51 mol% based on 1,4-dibromo-2,3-difluorobenzene) was added. After conducting the reaction at 45 C. for 4 hours, the reaction vessel was cooled with water and the reaction was stopped by adding 150 ml of 1N hydrochloric acid. The mixture was extracted with toluene, and the organic phase was washed with brine and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (developing solvent: toluene / hexane = 1: 1). The mixture was concentrated under reduced pressure, and the obtained residue was washed with 20 ml of hexane. The obtained residue was purified by recrystallization from heptane / toluene = 2/1 to obtain 1.88 g of 1,4-di (2-chlorothienyl-3 -) – 2,3-difluorobenzene as a colorless solid(Yield 45%).

According to the analysis of related databases, 156682-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOSOH CORPORATION; MIYASHITA, MASATO; WATANABE, MAKOTO; HACHIYA, HITOSHI; TANABIKI, MASAO; (26 pag.)JP2017/226629; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 52548-00-2, 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 52548-00-2 as follows.

PREPARATIVE EXAMPLE 44; .Ph In aBH4; Step i; A mixture of 3-bromo-6-fluoro-o-xyle?e (25.37g, 432 mmol) in anhydrous CCI4 (250 mL) was treated with NBS (44.5g, 864 mmol) and benzoyl peroxide (310 mg) and then heated at reflux overnight. The mixture was cooled to 0 C and filtered, washing with hexanes. The filtrate was concentrated and chromatographed (hexanes) to give 44A as an colorless oil (41.57g, with minor mono-bromo impurities).

According to the analysis of related databases, 52548-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; MCCORMICK, Kevin D.; DONG, Li; BOYCE, Christopher W; DE LERA RUIZ, Manuel; ZHENG, Junying; WON, Walter S.; WO2010/42475; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 65185-58-2, These common heterocyclic compound, 65185-58-2, name is 2-Bromophenethylamine, 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 95 (4R,6R,7R)-1-(2-(2-bromo)phenyl)ethyl-4,7-di(tert-butyldimethyl-silyloxy)-4,5,6,7-tetrahydro-1H-indole-4,6-carbolacame (22). A solution of allylketone III-1 (example 2) (500 mg, 1.14 mmol) in dicloromethane (50 mL) was placed into a gas-washing bottle and cooled down to -78 C. in a dry ice bath. The mixture was then flushed with argon for 5 min, oxygen for 5 min and then with an oxygen/ozone mixture for 12 min The end of the reaction was indicated by a 5% potassium iodide/water solution turning orange, which was located at the exit. Afterwards, the reaction mixture was flushed for 10 min with argon to remove excess ozone. The gas-washing bottle was taken from the cooling bath and the content was slowly warming up to room temperature. The solvent was evaporated under reduced pressure to afford an oil (500 mg) which was dissolved in a 1:1 mixture of dichloromethane-acetic acid (2 mL). The resultant solution was treated at 0 C. with 2-(2-bromo)phenylethylamine (0.18 mL, 1.25 mmol) and it was stirred for 30 min The reaction mixture was neutralized with powdered sodium bicarbonate and it was diluted with dichloromethane and water. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. All the combined organic extracts were dried (anh. Na2SO4), filtered and concentrated under reduced pressure. The obtained residue was purified by columm chromatography over silica gel, previously neutralized with triethylamine-hexanes (5:95), using diethyl ether-hexanes (5:95) as cluent to afford compound 22 (150 mg, 23%) as a colourless oil. [alpha]D20=-109.0 (c1.3, in CHCl3). 1H NMR (250 MHz, CDCl3) delta 7.60-7.50 (m, 1H, ArH), 7.15-7.07 (m, 2H, 2*ArH), 6.60-6.55 (m, 1H, ArH), 6.50 (d, J=2.7 Hz, 1H, H-2), 6.14 (d, J=2.7 Hz, 1H, H-3), 4.50 (dd, J=5.5 and 3.5 Hz, 1H, H-6), 4.18 (d, J=3.5 Hz, 1H, H-7), 4.07 (m, 2H, NCH2), 3.29-3.19 (m, 1H, CHHAr), 3.09-2.93 (m, 1H, CHHAr), 2.47 (d, J=10.5 Hz, H-5eq), 2.38 (dd, J=10.5 and 5.5 Hz, H-5ax), 0.97 (s, 9H, C(CH3)3), 0.88 (s, 9H, C(CH3), 0.22 (s, 3H, CH3), 0.18 (s, 3H, CH3), 0.14 (s, 3H, CH3) and 0.14 (s, 3H, CH3) ppm. 13C NMR (63 MHz, CDCl3) delta 175.9 (C), 137.2 (C), 132.6 (CH), 130.8 (CH), 128.7 (CH), 127.9 (CH), 124.7 (C), 123.8 (C), 123.4 (C), 121.2 (CH), 103.5 (CH), 76.5 (CH), 74.2 (C), 64.1 (CH), 46.5 (CH2), 38.3 (CH2), 38.2 (CH2), 25.7 (2*C(CH3)3), 18.2 (C(CH3)3), 18.0 (C(CH3)3), -2.9 (CH3), -3.0 (CH3), -4.1 (CH3) and -4.3 (CH3) ppm. IR (KBr) 1799 (C=O) cm-1. MS (CI) m/z (%) 606 and 608 (MH-). HRMS calcd for C29H45O4NSi281Br (MH+): 608.2050; found, 608.2043.

Statistics shows that 2-Bromophenethylamine is playing an increasingly important role. we look forward to future research findings about 65185-58-2.

Reference:
Patent; UNIVERSIDADE DE SANTIAGO DE COMPOSTELA; US2011/313032; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary