Category: bromides-buliding-blocks

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 103273-01-4 as follows. Formula: C10H14BrN

General procedure: A Schlenk tube containing Pd(OAc)2 (24.3 mg, 0.108 mmol), K2CO3 (759mg, 5.49 mmol), tricyclohexylphosphine (61.7 mg, 0.220 mmol), anddiphenylacetylene (470 mg, 2.58 mmol) was flushed with N2. NMP (21mL) and 2-bromo-5-tert-butylaniline (525 mg, 2.30 mmol) was added andthe resulting mixture was heated to 110 C. After stirred for 18 h, themixture was cooled to room temperature and then filtered through a shortpad of Celite with EtOAc. The eluent was washed with water and brine,dried over anhydrous Na2SO4, and evaporated to dryness. Purification bysilica-gel column chromatography (hexane/EtOAc as an eluent) afforded1a (460 mg, 1.42 mmol) in 62% yield.

According to the analysis of related databases, 103273-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shigeno, Ami; Matsuno, Takashi; Hiroto, Satoru; Shinokubo, Hiroshi; Chemistry Letters; vol. 44; 12; (2015); p. 1703 – 1705;,
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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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H2BrF3

To a solution of (ls,3s)-3-(4-fluorophenyl)cyclobutanol (0.13 g, 0.782 mmol, 1 equiv) and 5-bromo-l,2,3-trifluorobenzene (0.198 g, 0.939 mmol, 1.2 equiv) in DMF (8 mL) was added 60% NaH (0.038 g, 0.939 mmol, 1.2 equiv). After 1 h, the reaction was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried (NaiSOr) and concentrated in vacuo. The crude product was purified by silica gel flash chromatography (0-30% EtO Ac/hexane) to provide 5-bromo-l,2-difluoro-3-((3-(4- fluorophenyl)cyclobutoxy)benzene (0.17 g, 61%) as a colorless oil. NMR (500 MHz, CDCb) d 7.26 – 7.20 (m, 2H), 7.07 – 7.01 (m, 2H), 6.98 (ddd, J= 9.3, 6.1, 2.3 Hz, 1H), 6.83 (dt, J= 6.3, 2.2 Hz, 1H), 4.69 (quin, J= 7.2 Hz, 1H), 3.24 – 3.11 (m, 1H), 3.04 – 2.92 (m, 2H), 2.40 – 2.29 (m, 2H).

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; GILLIS, Eric P.; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M.; (367 pag.)WO2019/244066; (2019); A2;,
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Related Products of 17247-58-4, 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. 17247-58-4, name is (Bromomethyl)cyclobutane, This compound has unique chemical properties. The synthetic route is as follows.

A stirred solution of the ketimime 1a’ (50 g, 187.1 mmol, available from Aldrich Chemical Company, Milwaukee, Wis.) under N2 in dry THF (400 mL) was cooled to -78 C. and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv.) in THF. The reaction mixture was warmed to 0 C. and stirred for 1 h and treated with bromomethylcyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et2O (300 mL) and treated with aq. HCl (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et2O (1 L). The aqueous layer was made basic to pH12-14 with aq. NaOH (50%) and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give pure amine (1b’, 18 g) as a colorless oil.

The chemical industry reduces the impact on the environment during synthesis (Bromomethyl)cyclobutane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Schering Corporation; US2007/10431; (2007); A1;,
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Reference of 25017-13-4, A common heterocyclic compound, 25017-13-4, name is 1-(2-Bromoethyl)-3-fluorobenzene, molecular formula is C8H8BrF, 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 2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethanesulfonic acid 4-cyano- benzylamide dihydrochloride (0.127 g, 0.30 mmol; prep P above), 1-(2- bromo-ethyl) -3-fluoro-benzene (0.064 g, 0.315 mmol) and potassium carbonate (0.145 g, 1.05 mmol) was added acetonitrile (4 mL) and water (0.1 mL). The mixture was stirred for 20 minutes before it was heated by microwave irradiation (10 minutes, 160C) and was then filtered and evaporated. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 43 mg (30.3%) of the title compound. ¹3C NMR (125.7 MHz, CDCl3) 8 163.90,161.94, 144.35,141.66, 132.65, 130.03,129.96, 128.11,123.86, 118.70,115.12, 114.95,113.51, 113.34, 111.76, 68.34, 60.85, 56.85, 56.41, 54.40, 47.82, 47.47, 31.35

The synthetic route of 25017-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/123748; (2005); A1;,
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Electric Literature of 393-37-3, 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. 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(4-fluorophenyl)ethanol (1.02 g, 7.31 mmol, 1.2 equiv) in DMF (20 mL) was added KOtBu (0.96 g, 5.99 mmol, 1.4 equiv) and 4-bromo-1-fluoro-2-(tnfluoromethyl)benzene (1.48 g, 6.09 mmol, 1.2 equiv). After stirring 2 h, the reactionwas dilute with ether. The ether solution was washed with water, brine, dried (Na2SO4),and concentrated in vacuo. The crude product was purified by silica gel flashchromatography (0-30% EtOAc in hexane) to provide the product (1.36 g, 62%) as awhite solid. ?H NMR (500 MHz, CDC13) 7.69 (d, J= 2.5 Hz, 1H), 7.57 (dd, J= 8.8, 2.5 Hz, 1H), 7.28 – 7.25 (m, 2H), 7.02 (t, J=8.3 Hz, 2H), 6.85 (d, J 8.8 Hz, 1H), 4.21 (t, J6.5 Hz, 2H), 3.12 (t,J 6.5 Hz, 2H).

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-2-fluorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); 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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2,2-dimethylpropane

B) 2-methoxy-3-neopentylpyridine Under an argon atmosphere, a solution of 1-bromo-2,2-dimethylpropane (14.8 mL) in diethyl ether (120 mL) was added dropwise to magnesium (3.15 g) at a slow refluxing rate. The reaction mixture was heated under reflux for 30 min, and the obtained solution was added dropwise to a solution of 3-bromo-2-methoxypyridine (4.43 g) and PEPPSI-SIPr (trade name) (805 mg) in THF (80 mL) at room temperature. The reaction mixture was stirred at room temperature for 30 min, and saturated aqueous ammonium chloride solution was added at room temperature. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound (4.24 g) as a pale-yellow oil.

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 630-17-1.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; SHIBUYA, Akito; EP2816023; (2014); A1;,
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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. 134168-97-1, name is 3-Bromo-5-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-5-fluoroaniline

To a solution of 3-bromo-5-fluoroaniline (CAS 134168-97-1) (1.0 g, 5.3 mmol) and 2,6-lutidine (2.8 g, 26.5 mmol) in anhydrous DCM (30 mL), was added dropwise 2-chloro-ethanesulfonyl chloride (CAS 1622-32-8) (1.0 g, 6.3 mmol) in DCM (5 mL) at r.t. The mixture was stirred at r.t. for 30 min, and compound 34-A (1.5 g, 16 mmol) was added and stirred for 1 h. Water (50 mL) was added, and the mixture was extracted with EtOAc (100 mL×2). The combined organic layers was washed with sat NaCl (50 mL), dried over Na2SO4, concentrated, and purified by column to give the product (700 mg, yield 37%).

The synthetic route of 134168-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Huifen; Crawford, Terry; Harris, Seth F.; Magnuson, Steven R.; Ndubaku, Chudi; Wang, Lan; US2013/324516; (2013); A1;,
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Synthetic Route of 14922-91-9, The chemical industry reduces the impact on the environment during synthesis 14922-91-9, name is 5-Bromo-2-ethylaniline, I believe this compound will play a more active role in future production and life.

To a stirred mixture of 5-bromo-2-ethylaniline (3.39 g, 200 mmol) in distilled water (1 10 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3 x 50 ml), and the organic phase is washed with 1 M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2 x 30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2-iodobenzene (4.90 g) is furnished as an orange liquid.

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-2-ethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2009/150093; (2009); A1;,
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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 13633-25-5 as follows. Recommanded Product: 1-Bromo-4-phenylbutane

General procedure: To a solution of 4a-4e (0.1 mmol) in dry DCM (5 mL) was addedDIPEA (0.17 mmol) in a Schlenk tube. The tube was screwed down,stirred and heated at 75 C for 10 min, and the reaction mixturewas cooled to room temperature and benzyl bromide (1.7 mmol)was added to the solution. The reaction mixture was stirred andheated at 75 C for 48 h. After cooling the mixture, silica gel wasadded to the crude mixture, the solvent was evaporated underreduced pressure and the residue was purified by flash chromatography with a mixture of hexanes/EtOAc/TEA (95:5:1).

According to the analysis of related databases, 13633-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Djigoue, Guy Bertrand; Kenmogne, Lucie Carolle; Roy, Jenny; Maltais, Rene; Poirier, Donald; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5433 – 5451;,
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2695-48-9, name is 8-Bromo-1-octene, 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: C8H15Br

Schlenk flask was charged with 10·2BH3 (1.05 g, 3.62 mmol) and THF (15 mL), and cooled to -78 C. Then n-BuLi (2.5 M in hexanes, 6.4 mL, 16.0 mmol) was added with stirring. After 30min, Br(CH2)6CH=CH2 (2.80 g, 14.65 mmol) [S10] was added to the pale yellow solution over10 min. After 1 h, the cooling bath was removed. After 16 h, a 31P{1H} NMR spectrum showedthe consumption of 10·2BH3, and water (10 mL) was added. The aqueous phase was extractedwith Et2O (4 × 10 mL), and the combined organic layers dried (MgSO4) and filtered. The solventswere removed by rotary evaporation and the residue chromatographed (SiO2 column, 4 cm× 30 cm, hexanes). The solvent was removed from the product containing fractions by rotaryevaporation to give 11·2BH3 (0.476 g, 0.652 mmol, 18%) as a colorless oil.

The synthetic route of 2695-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fiedler, Tobias; Barbasiewicz, Micha?; Stollenz, Michael; Gladysz, John A.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2354 – 2365;,
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