Tag: M.W=200-300

Related Products 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 1 Synthesis of Compound M1 (Step (1a)) Under an argon gas atmosphere, 3,5-dibromo-4-methylaniline (47.0 g, 177 mmol), 35 wt % hydrochloric acid (111 ml) and ion exchanged water (111 ml) were mixed in a 1000 ml flask and cooled in an ice bath, and a solution prepared by dissolving sodium nitrite (12.9 g, 186 mmol) in ion exchanged water (about 130 ml) was dropped into the cooled mixture over a period of about 30 minutes. After completion of dropping, the mixture was stirred at room temperature for about 1 hour, then, cooled in an ice bath again, then, a solution prepared by dissolving potassium iodide (30.9 g, 186 mmol) in ion exchanged water (about 130 ml) was dropped into the cooled mixture over a period of 30 minutes. After completion of dropping, the mixture was stirred at room temperature for about 3 hours, then, added slowly to a separately prepared 10 wt % sodium hydrogen carbonate aqueous solution (about 1200 ml) while stirring. Ethyl acetate (about 1000 ml) was added and extraction was performed, the organic layer was washed with a 10 wt % sodium sulfite aqueous solution (about 450 ml), dried over anhydrous magnesium sulfate (50 g), filtrated, and the filtrate was concentrated to obtain a coarse product (77 g). The above-described coarse product was dissolved in acetone (750 ml), activated carbon (10 g) was added and stirred, then, the mixture was filtrated, and the filtrate was concentrated. It was again dissolved in acetone (750 ml), activated carbon (20 g) was added and stirred, then, the mixture was filtrated, and the filtrate was concentrated, and the deposited solid was dried under reduced pressure to obtain a yellow-brown solid (about 50 g). The resultant solid was dissolved in hexane, and ethanol was added to the solution to cause crystallization, and the resultant crystal was filtrated, and dried under reduced pressure, to obtain an intermediate 2,6-dibromo-4-iodotoluene (28.4 g, yield 43%, compound M1a) as a white crystal. 1H-NMR (300 MHz, CDCl3) delta (ppm)=2.51 (s, 3H), 7.83 (s, 2H)

The synthetic route of 13194-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US2011/272686; (2011); A1;,
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These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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. Safety of 1,4-Dibromo-2,5-difluorobenzene

Under a nitrogen atmosphere, 200 ml Schlenk reaction vessel, 1, 4 – dibromo – 2, 5 – difluorobenzene (wako pure medicine industry) was added 80 ml (22.0mmol) (dehydration grade) and THF 5.98 g. The solution was cooled to 0 C, ethyl magnesium chloride (sigma-Aldrich -, 2.0M) 13.0 ml of the solution were dropped THF (26.0mmol). The mixture 10 minutes at 0 C aged. The resulting solution was added to copper (II) chloride (wako pure medicine industry) 3.89 g (29.0mmol), was stirred at room temperature for between 3. 40 ml water was added to stop the reaction container 1N hydrochloride. Extracted with toluene, the organic phase was washed with brine, dried over anhydrous sodium sulfate. Concentration under reduced pressure, the residue obtained by removing the low-boiling component from the eluent used 4, 4 ‘- dibromo – 2, 2′, 5, 5’ – 2.98 g (71% yield) of a pale yellow solid obtained tetra- fluoro biphenyl.

The synthetic route of 1,4-Dibromo-2,5-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOSOH CORPORATION; MIYASHITA, MASATO; WATANABE, MASATO; (24 pag.)JP2017/160156; (2017); A;,
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Related Products of 68322-84-9, 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 68322-84-9 as follows.

EXAMPLE 7 Preparation of 3-[(2-Fluoro-5-(trifluoromethyl)phenyl]ethynyl]aniline A multinecked flash as described in Example 1 was charged with 4.93 g (0.020 mol) of 3-bromo-4-fluorobenzotrifluoride, 75 ml of dried, degassed triethylamine, 2.34 g (0.020 mol) of 3-aminophenylacetylene, 0.06 g (0.08 mmol) of bis(triphenylphosphine) palladium II chloride, 0.118 g (0.45 mmol) of triphenylphosphine, and 0.06 g (0.31 mmol) of cuprous iodide. The reaction mixture was heated at 70 C. for 40 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble hydrobromide salt followed by concentration of the filtrate gave the crude product (5.5 g, 89%) as an orange liquid. Short path distillation of the crude product under reduced pressure gave 4.05 g (0.014 mol, 70% yield) of the product as a yellow solid.

According to the analysis of related databases, 68322-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; National Starch and Chemical Investment Holding Corporation; US5107026; (1992); A;,
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Related Products of 2606-51-1, 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. 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1 ,5-a]pyrazin-8(7/-/)-one (100 mg, 429 mol) in dry DMF (2 mL) was added Cs2C03 (279 mg, 858 Mmol) and 5- (bromomethyl)benzo[d][1 ,3]dioxole (138 mg, 643 imol). The mixture was bubbled with 2 for 2 min and heated at 60C for 16 hours. The mixture was concentrated. DCM (30 mL) was added to the residue. It was filtered and the filter cake was washed with DCM (20 mL). The filtrate was concentrated and purified by flash chromatography on silica gel (10%~100% ethyl acetate in petroleum ether) to give 7-(benzo[d][1 ,3]dioxol-5-ylmethyl)-6-methyl-3- (tetrahydro-2H-pyran-4-yl)imidazo[1 ,5-a]pyrazin-8(7/-/)-one (81.74 mg, 52% yield). (1018) 1H NMR (CDCIa 400 MHz): delta 7.92 (s, 1 H), 6.76 – 6.69 (m, 4H), 5.95 – 5.93 (m, 2H), 5.13 (s, 2H), 4.14 – 4.11 (m, 2H), 3.61 – 3.55 (m, 2H), 3.10 – 3.05 (m, 1 H), 2.21 (s, 3H), 2.20 – 2.10 (m, 2H), 1.90 – 1.86 (m, 2H). (1019) LC-MS: fR = 2.245 min (method 3), m/z = 368.2 [M + H]+.

The chemical industry reduces the impact on the environment during synthesis 5-(Bromomethyl)benzo[d][1,3]dioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2018/78042; (2018); A1;,
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Reference of 5003-71-4, 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. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-bromopropylamine hydrobromide (1.0 g, 4.6 mmol) in a 2:1 dioxane/H2O (45 mL) was cooled to 0 C. and treated with K2CO3 (6.22 g, 45 mmol) and di-tert-butyl dicarbonate (1.5 g, 6.9 mmol). The reaction was stirred for 15 h while warming to room temperature. The dioxane was removed in vacuo and the remaining aqueous mixture was acidified with 5 N HCl and extracted with ethyl acetate (5*25 mL). The combined organic layers were dried with MgSO4 and yielded 3-bromo-N-(tert-butoxycarbonyl)propylamine as a colorless oil (0.93 g, 93%). 1H-NMR (CDCl3/TMS, ppm): 1.41 (s 9H, CH3), 2.02 (quintet, J=6.4 Hz, 2H, CH2), 3.23 (m, 2H, NCH2), 3.41 (t, J=6.6 Hz, CH2Br), 4.8 (broad, 1H, NH); 13C-NMR (CDCl3, ppm): 28.3 (CH3), 30.7, 32.6, 38.9 (CH2), 79.3 (quaternary C), 155.9 (CO); MS (CI, m/z): 239, 241 (M+H+ Calc. for C8H16BrNO2 237.03644).

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, 3-Bromopropan-1-amine hydrobromide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Research Development Foundation; US6703384; (2004); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

[000821j To a stirred solution of compound 1 (2 g, 1 eq) in THF (40 mL), CDI (2.42 g, 1.5 eq) was added and heated to reflux for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate (100 mL) and washed with water. Organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the crude compound 2. LCMS (mlz): 226.90 (M + 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Product Details of 1435-51-4

A solution of 28 (15.6 g, 0.05 mol) in Et2O (30 mL) was added dropwise at -78 C to a stirred solution of LDA, freshly prepared from diisopropylamine (5.5 g, 0.55 mol) and nBuLi (10 M, 5 mL, 0.05 mol) in THF (80 mL). After ca 30 min stirring at ca -78 C chlorodimethylsilane (5.0 g, 0.053 mol) was added slowly. The mixture was stirred for 30 min at -78 C and then was allowed to warm warm to ca. -50 C. 1 M aqueous H2SO4 (30 mL) was added with stirring. The organic phase was separated. The water phase was washed with Et2O (2 × 30 mL). The combined organic phase was dried over anhydrous MgSO4. It was filtered and evaporated under reduced pressure and the residue was subjected to a fractional distillation under reduced pressure. The crude product was obtained as a colorless liquid, b.p. 95-103 C (1 Tr). It tends to solidify partly when stored for a longer time at room temperature. Subsequent crystallization of this material from cold methanol (50 mL, -30 C) afforded pure product as a white solid, m.p. 28-30 C. Yield 13.5 g (73%). 1H NMR (400 MHz, CDCl3): delta 7.59 (s, 1H, Ph), 4.80-4.63 (m, 2H, SiH), 0.44 (dd, J = 3.9, 1.9 Hz, 12H, SiMe2) ppm. 13C NMR (101 MHz, CDCl3): delta 170.85 (d, J = 244.5 Hz), 132.84 (d, J = 3.5 Hz), 132.18 (d, J = 14.4 Hz), 124.42 (d, J = 38.8 Hz), -3.23 (d, J = 4.4 Hz) ppm. 19F NMR (376 MHz, CDCl3): delta -77.55 (m) ppm. Anal. Calcd for C10H15Br2FSi2 (370.20): C, 32.44; H, 4.08. Found: C, 32.23; H, 3.93.

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:
Article; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
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Synthetic Route 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.

Step A4-bromo-2-chloro-6-(trifluoromethyl)aniline[00296] 4-bromo-2-(trifluoromethyl)aniline (12.2 g, 50.8 mmol) was dissolved in acetonitrile (200 mL) before N-chlorosuccinimide (7.47 g, 55.9 mmol) was added and the mixture heated to 80 C. The reaction was stirred for 2 hours and allowed to cool to room temperature. The reaction mixture was quenched with water and extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue passed through a silica plug eluting with dichloromethane. The filtrate was concentrated to give the title compound (13.1 g, 94%) as a liquid. H NMR (400 MHz, DMSO- /6) delta ppm 7.78 (d, 1 H), 7.52 (d, 1 H), 5.92 (s, 2 H).

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; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John G; FANG, Jing; PEAT, Andrew James; TAI, Vincent; TURNER, Elizabeth; WO2011/97491; (2011); A1;,
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Reference of 1337523-99-5, A common heterocyclic compound, 1337523-99-5, name is 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine, molecular formula is C10H12BrN, 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.

In a 50-mL round-bottom flask, to a solution of 6-bromo-l ,2,3,4-tetrahydronaphthalen-l -amine (4.34 g, 19.17 mmol, 1.00 equiv) and TEA (3.07 g, 30.33 mmol, 1.58 equiv) in dichloromethane (80 mL) was added (Boc)20 (6.65 g, 30.47 mmol, 1.59 equiv) at 0 C. The resulting solution was stirred for 16 h at 25 C. After the reaction was done, it was quenched by the addition of water (10 mL) and the mixture was extracted with dichloromethane (3 x 20 mL). The combined organic layers were washed by brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with dichloromethane in petroleum ether (5% to 20% gradient) to afford tert-butyl N-(6-bromo-l, 2,3,4- tetrahydronaphthalen-l -yl)carbamate as white oil (6.2g, 95% for two steps). MS: m/z = 269.9[M+H-56]-

The synthetic route of 1337523-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; CALDWELL, Richard; LIU-BUJALSKI, Lesley; POTNICK, Justin; NEAGU, Constantin; KULKARNI, Shashank; JONES, Reinaldo; QIU, Hui; (238 pag.)WO2020/43638; (2020); A1;,
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These common heterocyclic compound, 58971-11-2, name is 3-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. name: 3-Bromophenethylamine

General procedure: 4-[(Ethoxycarbonyl)amino]butanoic acid (12a, 700 mg, 4mmol) was dissolved in an hydrous dichloromethane (14 mL) under argon atmosphere. The solution was cooled to 0 C. Triethylamine (1.2 mL, 870 mg, 8.6 mmol) and 3-fluorophenethylamine (0.6 mL, 4.6 mmol) were added consecutively. Afterwards EDC-HCl (900 mg, 4.7 mmol)was added in one portion. Catalytic amount DMAP (30 mg)was added, the resulting mixture was stirred for 1 h at 0 C and then for 16 h at room temperature. The reaction mixture was diluted with dichloromethane (30 mL) and consecutively washed with 1M HCl, saturated NaHCO3 solution and water (20 mL of each). The combined extracts were dried (Na2SO4) and evaporated to give an oily residue.The crude product was crystallized from hexane

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

Reference:
Article; Ahamed, Muneer; Vermeulen, Koen; Schnekenburger, Michael; Moltzau, Lise Roman; Levy, Finn Olav; Marton, Janos; Froeyen, Mathy; Olberg, Dag Erlend; Diederich, Marc; Bormans, Guy; Letters in drug design and discovery; vol. 14; 7; (2017); p. 787 – 797;,
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