Tag: M.W=100-200

Reference of 55289-36-6,Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Under nitrogen atmosphere, 3-bromo-2-methylaniline (5.01g, 26.9 mmol) was dissolved in DCM (100 mL). To this solution, cooled with ice bath, TEA (7.5 mL, 53.9 mmol) and 4-tert-butylbenzoyl chloride (5.3 g, 26.9 mmol) were added dropwise and stirred at 0 C for 4 h. The reaction mixture was diluted with DCM (100 mL), washed with water (2×30 mL), 1N hydrochloric acid solution (30 mL), saturated sodium hydrogen carbonate solution (30 mL) and brine (30 mL), then the organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was suspended in hexane, then the precipitate was collected by filtration, washed with hexane then dried to afford N-(3-bromo-2-methylphenyl)-4-(tert-butyl)benzamide (9.0 g). 1H NMR (400 MHz, DMSO-d6) delta 10.06 (s, 1H), 7.92 (d, J = 8.4 Hz, 2H), 7.54 (m, 3H), 7.33 (d, J = 7.7 Hz, 1H), 7.18 (t, J = 8.0 Hz, 1H), 2.27 (s, 3H), 1.32 (s, 9H).

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-2-methylaniline, its application will become more common.

Reference:
Patent; Carna Biosciences, Inc.; KAWAHATA, Wataru; ASAMI, Tokiko; SAWA, Masaaki; ASAMITSU, Yuko; IRIE, Takayuki; MIYAKE, Takahiro; KIYOI, Takao; EP2824099; (2015); A1;,
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These common heterocyclic compound, 2924-09-6, name is 5-Bromo-2-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. category: bromides-buliding-blocks

5-Bromo-2-fluoroaniline (2.85 g, 15.00 mmol) and 4-methylmorpholine (1.65 mL, 15.00 mmol) were dissolved in anhydrous dichloromethane (20 mL) and the solution was cooled to -20 C. Add compound 5 (3.55 g, obtained in the synthesis of steps 1-3,13.66 mol), the mixture was slowly warmed to 20 C and kept stirring at 20 C for 12 hours. The resulting red suspension was poured into water (80 mL). The phases were separated and the organic layer was dried with Na2SO4, filtered and evaporated.A red oil was obtained and the residual red oil was dissolved in methanol (20 mL).The solution was heated to reflux for 1 hour to form a precipitate. The mixture was cooled to 4 C.The precipitate was collected by filtration, washed with methanol and dried to give a pale pink solid.N-(5-Bromo-2-fluorophenyl)-6-(furan-2-yloxy)pyridine-3-sulfonamide (Compound 6), 3.50 g, yield 62%.

The synthetic route of 5-Bromo-2-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dou Yuling; (11 pag.)CN108484585; (2018); A;,
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Synthetic Route of 2270-59-9, 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. 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, This compound has unique chemical properties. The synthetic route is as follows.

1.55 kg of magnesium and 10 kg of THF are charged into a stainless steel reactor provided with liquid nitrogen cooling . This is heated under reflux (60-700C) and, still at that temperature, 0.5 I of the solution containing 10 kg of 5-bromo-2-methyl- pentene (II) at 100% is poured. This is kept under reflux for at least 10 minutes until the reaction starts. The reaction mixture is then cooled to 50-600C and, keeping it at that temperature with a brine bath, the remaining solution of 5-bromo- 2-methyl-pentene (II) in THF is poured. The reaction mixture is kept at 50-600C for at least 1.5 hours and 40 kg of THF are added. The reaction mixture is then cooled with liquid nitrogen to -65/-700C and at that temperature 7.2 kg of diethyloxalate are added. The reaction mixture is kept at -65/-700C for at least 1 hour, under EPO stirring. The mixture thus obtained is then poured into another enamelled reactor containing 10kg of 32% hydrochloric acid dissolved in 30 kg of demineralised water and previously cooled to 0-100C.The reaction mixture is then brought to 20-300C and left until the phases separate. The aqueous phase is removed, while the organic phase is washed at 20-300C with 0.25 kg of sodium bicarbonate dissolved in 5 kg of demineralised water. The reaction mixture is stirred at the same temperature and left until the phases separate. The lower aqueous phase is removed, while the solvent is removed from the organic phase by vacuum distillation until an oily residue is obtained. Then 15 kg of THF are added and the mixture obtained is stirred until a solution is obtained which is sent to the next stage. Yield not determined.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-methylpent-2-ene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ERREGIERRE S.p.A.; STRAGEN PHARMA SA; WO2007/9953; (2007); A1;,
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Reference of 2550-36-9, 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. 2550-36-9, name is (Bromomethyl)cyclohexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

20 g of bromomethyl cyclohexane,After 12.5 g of 1-naphthol was dissolved in 300 g of NMP in a three-necked flask,12g of potassium carbonate was added,14g potassium iodide was heated at 120 C for 8 hours.In the reaction solution was added 300g of water,Extraction was performed three times with 100 g of hexane,The resulting organic layers were combined,Washed once with 100 g of 1 N aqueous sodium hydroxide solution,Water 100g washed once,Brine 100g washed once,Concentration gave 13 g of compound 1.

The synthetic route of (Bromomethyl)cyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM CORPORATION; SHIRAKAWA, MICHIHIRO; TANGO, NAOHIRO; SHIBUYA, AKINORI; YAMAGUCHI, SHUHEI; KATAOKA, SHOHEI; (175 pag.)TWI579263; (2017); B;,
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Synthetic Route of 766-46-1, These common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, 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: An oven dried 20 mL glass vial was charged with PdCl2(PPh3)2 (28.1 mg, 0.04 mmol), CuI (7.6 mg, 0.04 mmol), acid chloride (2.60 mmol), terminal alkyne (2.00 mmol) and anhydrous triethylamine (10 mL). The vial was flushed with nitrogen and sealed with a pressure relief cap. The reaction mixture was stirred at room temperature, overnight, until the disappearance of starting material was observed, as monitored by thin layer chromatography. The reaction mixture was diluted with diethyl ether (40 mL) and washed with brine (40 mL). The aqueous phase was then extracted with diethyl ether (2 x 20 mL). The combined organic layers were dried over anhydrous MgSO4, and concentrated using a rotary evaporator under reduced pressure (20 mmHg). The resulting residue was purified by flash column chromatography on silica gel (eluent: hexanes/ethyl acetate).

The synthetic route of 766-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Xiaochen; Hong, Dongsub; She, Zhigang; Hersh, William H.; Yoo, Barney; Chen, Yu; Tetrahedron; vol. 74; 45; (2018); p. 6593 – 6606;,
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Adding a certain compound to certain chemical reactions, such as: 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, belongs to bromides-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 51376-06-8, Computed Properties of C6H3BrN2O

5-bromo-2,1,3-benzoxadiazole (0.71 g), cesium carbonate (1.4 g), 2,2′- bis(diphenylphosphino)-1,r-binapthyl (0.17 g) and Tris-(dibenzylideneacetone) dipalladium(O) (0.13g) were added to a solution of (5S)-3-[3-fluoro-4-(piperidin-4- yloxy)phenyl]-5-[(isoxazol-3-ylamino)methyl]-1,3-oxazolidin-2-one (1.3 g) (obtained from Step b) in dry dimethylformamide (15 mL) and the reaction mixture was heated at 100 C for about 17 hours. The reaction mixture was filtered and the solvent was evaporated. The crude product thus obtained was purified by column chromatography using 1 % methanol in dichloromethane to yield the title product (0.07g).Melting point: 75-100 C; EIMS (m/z): 534.21; 1HNMR(DMSO): delta 8.16 (s, 1H), 7.66 (d, 1H), 7.48 (dd, 1H), 7.3 (m, 2H), 7.17 (d, 1H), 7.08-7.05 (t, 1H), 6.75 (s, 1H), 4.99 (m, 1H), 4.53 (m, 3H), 4.14-4.11 (t, 1H), 3.95 (t, 1H), 3.61 (m, 2H), 3.3 (m, 2H), 2.04 (m, 4H).

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, 5-Bromobenzo[c][1,2,5]oxadiazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); 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. 5433-01-2, name is 1-Bromo-3-isopropylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 5433-01-2

Preparation Example 1-1: Preparation of 4-t-butyl-N- (4- isopropylphenyl ) benzenamine; As represented below in Reaction Scheme 1, 25g of 3-t- butylaniline (0.125mol) and 37.3g of 3-bromoisopropylbenzene(0.25mol) were dissolved in 25OmL of toluene, and 3.43g ofPd2(dba)3 (0.0037mol) was added thereto under a nitrogen atmosphere. Then, 14.4g of NaOBufc (0.15mol) and 1.157g of (t- Bu)3P (0.0075mol) were added to the reaction solvent, and the reaction mixture was refluxed and stirred for 12 hours. The reaction mixture was checked for the completion of the reaction by means of TLC, and if the reaction was completed, the reaction product was cooled down to room temperature. The reacted solution was poured onto a thin silica pad to perform short chromatography, and then was washed with methylene chloride (MC) . The washed solution was subjected to distillation under reduced pressure to thereby remove the solvent, and was chromatographed using n-hexane to thereby obtain a desired white solid product (29.4g, 88%). [Reaction Scheme 1]

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; DOOSAN CORPORATION; WO2009/91095; (2009); A1;,
Bromide – Wikipedia,
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Application of 10485-09-3, These common heterocyclic compound, 10485-09-3, name is 2-Bromoindene, 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.

(Comparative Example 3) 1.2 ml of a tetrahydrofuran solution of 0.25 g of magnesium was cooled to 0C, and 5.0 ml of a tetrahydrofuran solution of 1.0 g of 2-bromoindene was slowly dropped thereto.After the dropping, the mixture was stirred at the same temperature for 1 hour, and 0.57 g of 2,6- dimethylbenzaldehyde was added thereto, and stirred for 12 hours while the temperature was being raised to 25C.After the confirmation of the degree of reaction progress by TLC, the reaction was terminated with an ammonium chloride aqueous solution, and an organic phase was extracted with ethyl acetate.[0132] After the obtained organic phase was dried with anhydrous magnesium sulfate, the organic phase was concentrated and purified by column chromatography. Then, 5 g of manganese dioxide was added to 30 ml of a chloroform solution of the obtained intermediate compound, and the mixture was stirred at 25 C for 12 hours. After the confirmation of the degree of reaction progress by TLC, the manganese dioxide was filtered, and 0.42 g (yield: 40%) of Comparative Product 3 shown below was obtained by recrystallization. Thestructure of Comparative Product 3 was confirmed by 1HNMR. 1H-NMR (CDC13; TMS) : delta 2.21 (s, 6H) , 3.85 (s, 2H) , 7.07 (d, 2H) , 7.20-7.26 (m, 2H) , 7.33-7.41 (m, 2H) , 7.47 (d, 1H) , 7.58 (d, 1H)

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

Reference:
Patent; CANON KABUSHIKI KAISHA; SAITOH, Terunobu; WO2011/81078; (2011); A1;,
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Synthetic Route of 103-64-0, A common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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 round-bottom flask was charged with phenylacetylene (0.75 mmol, 0.08 mL), K2CO3 (0.75 mmol, 100 mg), PEG 200 (1 mL), and aryl halide (0.5 mmol). To this mixture, Pd(0) nano-catalyst supported on SDPP (1.5 mol-%, 3.0 mg) prepared according to our previous report [13] was added. In the case of aryl iodides and activated aryl bromides, the reaction mixture was placed in a 100 C oil bath; and in the case of the less active and deactivated aryl bromides and chlorides, the reaction mixture was placed in a 120 C oil bath. After completion of the reaction, the catalyst was removed by centrifugation and the remaining mixture was extracted with ethyl acetate (310 mL) and water several times and dried over anhydrous Na2SO4. The organic layer was evaporated under reduced pressure, and then purified by column chromatography over silica gel 60 (230-240 mesh; Merck) using petroleum ether/ethyl acetate (5 : 1) as eluent to afford the product with high purity in 51-95% yield. Note: This procedure can also be used, but the catalyst is prepared in situ by adding the appropriate amounts of SDPP and Pd(OAc)2.

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; Iranpoor, Nasser; Firouzabadi, Habib; Motevalli, Somayeh; Rajabi, Khashayar; Australian Journal of Chemistry; vol. 68; 6; (2015); p. 926 – 930;,
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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. 591-19-5, name is 3-Bromoaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6BrN

c. 3,4-Dibromoaniline. 3-Bromoaniline (3 g, 17.4 mmol) was dissolved in 15 ml CH2 Cl2 and the reaction mixture was cooled to -10 C. in an ice-salt bath. 2,4,4,6-Tetrabromo-2,5-cyclohexadienone, (9.29 g, 0.02 mmol) was added in small portions with constant stiting. The reaction mixture was stirred for a period of 7 hours at 0 C. after which the reaction was quenched with 2N NaOH (10 ml). The aqueous layer was extracted with CH2 Cl2 and the organic layer was dried over anhydrous Na2 SO4. The CH2 Cl2 layer was concentrated in vacuo and purified by column chromatography. Elution with 0-3% ethyl acetate/n-hexanes yielded 3.2 g (12.7 mmol, 73%) of pure product; mp 80-81 C.; IR (KBr) 3406, 3318, 3210, 1583, 1464, 1287, 1108, 860, 668; 1 H NMR (CDCl3) 6 6.49 (dd,1H,J=2.7,8.6), 6.7 (d,1H,J=2.64), 7.32 (d,1H,J=8.6); 13 C NMR (CDCl3) 6 112.6, 116, 120.1, 125.45, 134.26, 147.08.

The synthetic route of 591-19-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rutgers, The State University of New Jersey; US6063801; (2000); A;,
Bromide – Wikipedia,
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