Tag: M.W=200-300

Electric Literature of 142808-15-9, These common heterocyclic compound, 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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) S.S’-Difluoro-^-ttrifluoromethylH-biphenylamineTo a stirred solution of 2-fluoro-4-iodoaniline (7.0 g, 29.5 mmol), bis(pinacolato)diboron (9.8 g, 38.6 mmol) and potassium acetate (8.7 g, 88.6 mmol) in dimethylformamide (150 ml_) was added [1 ,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (0.66 g, 0.9 mmol). After purging with nitrogen, the reaction was heated to 80 0C and stirred for 4 h. 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (7.2 g, 29.6 mmol), potassium carbonate (10.2 g, 73.8 mmol), water (20 ml_) and [1 ,1’- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (0.66 g, 0.9 mMol) were added and the reaction stirred at 100 0C for 18 h. After cooling to room temperature, the reaction was evaporated to dryness under vacuum. The residue was taken up in ethyl acetate, filtered to remove insolubles, washed with water, brine, dried (Na2SO4), filtered and concentrated under vacuum. Purification by flash chromatography on silica gel (20% ethyl acetate/hexanes), trituration with hexane, filtration and drying under vacuum gave the title compound (4.93 g, 61 %) as a white solid: MS (ES) m/e 274.0 (M + H)+.

Statistics shows that 4-Bromo-2-fluorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 142808-15-9.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113432; (2006); A2;,
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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. 58971-11-2, name is 3-Bromophenethylamine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H10BrN

Intermediate (iv)N-[2-(3-Bromo-phenyl)-ethyl]-4-methyl-benzenesulfonamideTsCI (1 1 g, 57.5 mmol, 1 .15 eq.) was dissolved in DCM (150 ml_) and cooled to 0C. To this solution was added a solution of 3-bromo-phenethyamine (10 g, 50 mmol) in DCM (50 ml_), followed by Et3N (18 ml_). The solution was stirred at r.t. overnight when TLC (5% MeOH in DCM) showed that the reaction was complete. LCMS: t=4.158, MS 354/356. 3 g of polymer-supported-amine was added, stirred for 1 h at r.t. The solution was filtered through a Celite pad, rinsed with DCM and the solvent was evaporated to dryness, re-dissolved in DCM (100 mL) and water (20 mL). The two layers were separated, and the aqueous layer was extracted with DCM (20 mLx2). The combined DCM extracts were washed with 1 N H3PO4 (2 x 20 mL) and sodium bicarbonate (20 mL), and brine (15 mL x 2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with DCM (TLC: DCM) to get 17.89 g (100%) of the title compound as a off-white solid, on standing.TLC (DCM): 0.7Rf.LCMS: RT = 3.72 minutes, MS: 356 (M+H).

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 58971-11-2.

Reference:
Patent; SANOFI; GAO, Zhongli; HARTUNG, Ryan; WO2011/143155; (2011); A1;,
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61613-22-7, name is 2-Bromo-N-phenylaniline, 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. COA of Formula: C12H10BrN

2-Bromo-N-phenylaniline (10 g) was dissolved inAfter 100 ml THF (tetrahydrofuran), the reaction temperature is lowered to -78 C,20 ml of 2.5 M BuLi (butyllithium) was slowly added dropwise and stirred for 1 hour.Dissolving 15.2 g of bis(4-chlorophenyl)methanone (bis(4-chlorophenyl)methanone)After 150 ml of THF (tetrahydrofuran) was slowly added dropwise,The temperature was raised to room temperature and stirred for 12 hours. After the reaction is over,A solid obtained by extracting with distilled water and MC (dichloromethane) and removing water by using anhydrous magnesium sulfate and then filtering under reduced pressure is directly dissolved in 150 ml of acetic acid (Acetic acid) without further purification.10 ml of sulfuric acid was added dropwise and stirred under reflux. After the reaction is over,Extraction with distilled water and MC (dichloromethane) and column purification of the resulting solid10g I3. (yield 62%)

The synthetic route of 61613-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dongjin Shimeiken Co., Ltd.; Xian Haowan; An Xianzhe; Jin Bingyu; Han Zhengyou; Jin Jintai; (31 pag.)CN104471022; (2018); B;,
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Adding a certain compound to certain chemical reactions, such as: 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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 337915-79-4, name: 5-Bromo-N1-methylbenzene-1,2-diamine

To a solution of 42 mL of 6N HCI and 63 mL of water, 5-bromo-N1-methylbenzene- 1 ,2-diamine (9.1 g, 45.4 mmol) and glycolic acid (17.2 g, 227.2 mmol) was added sequentially. The mixture was heated to reflux for 2 hours. After cooling down to room temperature, the mixture was neutralized to PH 9 by ammonium hydroxide. Precipitate formed, filtered, rinsed by water and dried by vacuum to yield (6-bromo-1-methyl-1H- benzo[d]imidazol-2-yl)methanol (8.5 g). 400 MHz 1H NMR (CDCI3) delta 7.5 (d, 1 H), 7.46 (m, 1H), 7.35 (dd, 1 H), 4.92 (s, 2H), 4.74(b, 1 H), 3.8 (s, 3H); MS (M+1) 241 , 243

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-Bromo-N1-methylbenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12623; (2008); A1;,
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Related Products of 327-51-5,Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

1,4-dibromo-2,5-difluorobenzene (2.17 g, 10mmol), potassium carbonate (2.07 g, 15mmol), and palladium acetate (225 mg, 1.0mmol) were taken under argon atmosphere, and DMAc (30 mL) was added and suspended. Into this mixture, a pivalic-acid-toluene solution (1.03M, 2.9 mL, 3.0mmol) and a tri-cyclohexyl phosphine toluene solution (0.6M, 3.3 mL, 2.0mmol), 2-(4-propylcyclohexyl) thiazole (6.28 g, 30mmol, trans/cis=69/31) synthesized in reference example-2 was added, and it agitated at 150 degrees C for 65 hours. The mixed solvent (2:1) of chloroform and hexane was added to the reaction mixture after ending reaction, and it filtered using alumina. The rough product obtained by condensing a filtrate was ******ed from dichloromethane/hexane, and target 1,4 -bis [2-(trans-4-propylcyclohexyl) thiazole 5-yl]-2,5-difluorobenzene was obtained as a white solid (1.56 g, 30%).After silica gel column chromatography (eluate: hexane/chloroform) refines the solid obtained by condensing the filtrate of the above-mentioned recrystallization, by recrystallizing [ toluene ] by the 95%-ethanol following **, Target 1-[2-(trans-4-propylcyclohexyl) thiazole 5-yl]-4-[2-(cis-4-propylcyclohexyl) thiazole 5-yl]-2,5-difluorobenzene was obtained as a white solid (654 mg, 13%).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE; Aihara, Hidenori; kikuchi, Mai; Hachiya, Hitoshi; Watanabe, Makoto; (39 pag.)JP2017/66069; (2017); A;,
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Reference of 698-00-0, 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. 698-00-0, name is 2-Bromo-N,N-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry Schlenk tube under argon atmosphere was charged with the 2-bromo-N,Ndimethylaniline (1.99 g, 10 mmol) in degassed THF (15 mL). The solution was cooled at -78 C and n-BuLi (2,4 M in THF, 1.1 eq.) was added. The mixture was stirred for 30 min at -78 C and then, at 0 C for 15 minutes. Then PPh2Cl (1.93 mL, 10.5 mmol) neat was added at -78 C under an argon atmosphere. The white solution was filtered on a pad of celite, the solid was washed with pentane (20 mL), ether (20 mL) and CH2Cl2 (20 mL). 2-(diphenylphosphino)-N,N-dimethylaniline was obtained after purification by flash chromatography on silica gel (eluent : AcOEt / cyclohexane 10 / 90) as a white solid (1,67 g, 56%).

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-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pagnoux-Ozherelyeva, Anastassiya; Bolien, David; Gaillard, Sylvain; Peudru, Flavie; Lohier, Jean-Francois; Whitby, Richard J.; Renaud, Jean-Luc; Journal of Organometallic Chemistry; vol. 774; (2014); p. 35 – 42;,
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Synthetic Route of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

Method 6 4-Bromo-2,5-difluorobenzaldehyde To 1,4-dibromo-2,5-difluorobenzene (10.28 g, 37.81 mmol) in tetrahydrofuran (80 mL) at -40 C. was isopropylmagnesium chloride lithium chloride complex (29.1 mL, 37.81 mmol) added dropwise. After 1 h at -40 C. was N,N-dimethylformamide (58 mL, 756 mmol) added and the mixture was stirred for 30 minutes at -40 C. NH4Cl (2M, aq, 100 mL) was added and the mixture was extracted with ethyl acetate. The organic phase was dried with MgSO4 and concentrated to give 4-bromo-2,5-difluorobenzaldehyde (6.20 g, 74%) as a solid. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 10.28 (d, 1H) 7.61 (dd, 1H) 7.48 (dd, 1 H).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2010/267723; (2010); A1;,
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Reference of 941-37-7, 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 941-37-7 as follows.

To 100g of 1-bromo-3, 5-dimethyl adamantane and 86g of urea, adding 80ml of 80wt% formic acid, heating to 80C and holding for 3 hours. Cooling to the room temperature and adding 75ml of 85% phosphoric acid to hydrolyze at 80C for 1 hour. Adjusting with 10% potassium hydroxide aqueous solution to a pH of 12. Extracting with toluene twice, combining the organic layers and washing with water. Concentrating under reduced pressure to yield a limpid yellow solution as 1-amino-3,5-dimethyl adamantane crude. To the crude, adding 150ml of ethanol and concentrated hydrochloric acid, heating to dissolve and crystallizing to yield a white solid. Drying the solid and re-crystallizing with ethanol to yield 61.0g of pure Memantine Hydrochloride. The yield is 68.8% (GC 99.5%). 1HNMR (CDCl3, 400MHZ): delta0.833 (6H, singlet), 1.156 (2H, quartet), 1.328 (4H, quartet), 1.683(4H, quartet), 1.869 (2H, broad signal), 2.179 (1H, broad signal), 8.28 (3H, broad signal). MS (Q-Tof micro, ESI+): 179(M+), 164, 122, 108, 93 and 55. Element Analysis (C12H21N.HCl): actual results (calculated value%): C 66.77 (66.80), H 10.40 (10.28), N 6.48(6.49) and Cl 16.39(16.43)

According to the analysis of related databases, 941-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; Zhejiang Kangyu Pharmaceutical Co., Ltd.; EP1674446; (2006); A1;,
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327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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. Quality Control of 1-Bromo-2,4,5-trifluorobenzene

In an oven-dried flask, dried halogen-group-containing compounds (2.3 equiv) were added to dry THF containing magnesium metal (Mg) (2.3 equiv, with glass pieces to activate the magnesium metal) at room temperature under nitrogen. The reaction mixture was stirred vigorously until Grignard generation occurred. The lactone (1 equiv dissolved in 40 mL of THF) was added dropwise to the Grignard reagent solution, and the mixture was stirred at room temperature for 16 h and monitored by TLC. The mixture was treated with saturated aqueous NH4Cl (20 mL) and then extracted with AcOEt (3¡Á10mL). The combined organic phases were dried over Na2SO4 and the solvent was removed by an evaporator. The residue was purified by silica-gel column chromatography (AcOEt/hexane). In another experiment, the ring-opening reactions of homoserine lactone with select Grignard reagents were carried out using 2.7 equiv ArMgBr at r.t. and 50C for 2 h.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guendo?du, Oezlem; Turhan, P?nar; Koese, Aytekin; Altunda?, Ramazan; Kara, Yunus; Tetrahedron Asymmetry; vol. 28; 9; (2017); p. 1163 – 1168;,
Bromide – Wikipedia,
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Application of 61613-22-7, A common heterocyclic compound, 61613-22-7, name is 2-Bromo-N-phenylaniline, molecular formula is C12H10BrN, 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.

Under an Ar atmosphere, to a 500 ml, three-neck flask, Compound C (5.00 g) was put and dissolved in dehydrated THF (100 ml), and nBuLi (1.6 M in hexane, 12.6 ml) was added dropwise thereto at about -78 C. After stirring at about -78 C. for about 1 hour, a THF solution (100 ml) of B (7.01 g) was added dropwise thereto, followed by stirring for about 16 hours while gradually increasing the temperature to ambient temperature. Water was added to the resultant product, and an organic layer was extracted with CH2Cl2, separated, and dried with MgSO4. Solvents were removed by distillation under a reduced pressure. The crude product thus obtained was dissolved in toluene (100 ml), and pTsOH (11.5 g) was added thereto, followed by heating and stirring at about 80 C. for about 6 hours. After the reaction, a precipitate thus produced was obtained by filtering and separated by recrystallization to obtain 6.24 g (yield 62%) of Intermediate D. The molecular weight of Intermediate D measured by FAB-MS was 499.

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; SAMSUNG DISPLAY CO., LTD.; SAKAMOTO, Naoya; AKASHI, Nobutaka; (46 pag.)US2020/20866; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary