Category: bromides-buliding-blocks

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. 626-88-0, name is 1-Bromo-4-methylpentane, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-4-methylpentane

General procedure: A Grignard suspension of 1-bromo-4-methylpentane in THF (50 mL) was prepared from the bromide (1.64 g, 9.94 mmol) and Mg (0.29 g, 11.92 mmol) in the usual manner. The suspension was cooled (-50 C) and Cu(I) bromide (0.712 g, 4.97 mmol) was added to it. The mixture was stirred for 15 min. To the resultant black suspension at -50 C was added compound 8a (1.5 g, 3.31 mmol) in THF (40 mL). The mixture was stirred at the same temperature for 1 h and then overnight at room temperature. The reaction was quenched by the addition of aqueous saturated NH4Cl (10 mL) and extracted with EtOAc. The organic layer was washed with 5% aqueous HCl, water, brine, and then dried over Na2SO4. Solvent removal under reduced pressure and column chromatography of the residue (silica gel, 0-10% EtOAc in hexane) afforded pure 9a (1.24 g, yield 70%) as a colorless liquid.

The synthetic route of 626-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dubey, Akhil Kumar; Chattopadhyay, Angshuman; Tetrahedron Asymmetry; vol. 22; 14-15; (2011); p. 1516 – 1521;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 418762-26-2, The chemical industry reduces the impact on the environment during synthesis 418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, I believe this compound will play a more active role in future production and life.

Intermediate 11 2-fluoro-5-methyl-4-(l,4-dioxaspiror4.51dec-7-en-8-vl)anirine [0092] A mixture of 4,4,4,4-tetramethyl-2-(l,4-dioxaspiro[4.5]dec-7-en-8-yl)- 1,3,2-dioxaborolane (532.0 mg, 2.0 mmol), 4-bromo-2-fluoro-5-methylaniline (406.0 mg, 2.0 mmol), tetrakis(triphenylphosphine)palladium(0) (231.1 mg, 0.2 mmol), cesium fluoride (912.0 mg, 6.0 mmol), 1,2-dimethoxyethane (4 mL) and methanol (2 niL) was degassed for 5 min and then heated at 130C in a microwave reactor for 15 min. The reaction was concentrated in vacuo, and purified by silica chromatography (EtOAC / Hexanes: 3/7) to afford 2-fluoro-5-methyl-4-(l,4-dioxaspiro[4.5]dec-7-en- 8-yl)aniline; ESMS m/z 264.1 (M + H+).

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, 4-Bromo-2-fluoro-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 13194-73-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13194-73-5 name is 3,5-Dibromo-4-methylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step A: 2,6-Dibromo-4-iodotoluene To a solution of 3,5-dibromo-4-methylaniline (4.17 g, 15.74 mmol) in CH2I2 (10 mL) was added tert-butylnitrite (3.0 mL, 23.61 mmol) slowly at 0 C. while stirring vigorously. The ice bath was removed and the reaction mixture was stirred at rt while the reaction was very exothermic, then placed it in a 80 C. oil bath and heated for 20 min. CH2I2 was distilled off under high vacuum, and the remaining residue was purified by flash chromatography eluding with 100% hexane to gave the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dibromo-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Doherty, James B.; Stelmach, John E.; Chen, Meng-Hsin; Liu, Luping; Hunt, Julianne A.; Ruzck, Rowena D.; Goulet, Joung L.; Wisnoski, David D.; Natarajan, Swaminathan Ravi; Rupprecht, Kathleen M.; Bao, Jianming; Miao, Shouwu; Hong, Xingfang; Sinclair, Peter J.; Kallashi, Florida; US2003/92712; (2003); A1;,
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. 50670-49-0, name is 4-Bromo-4′-methyl-1,1′-biphenyl, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-4′-methyl-1,1′-biphenyl

The reaction mixture containing compound 3 (300 mg, 0.456 mmol,tetrahydrate), 4-methylphenylboronic acid (248 mg, 1.82 mmol), K2CO3(251 mg, 1.82 mmol), and PdCl2(PPh3)2 (38 mg, 0.055 mmol) in EtOH/H2O (5/1; 6 mL) was stirred at 50 C for 4 h under a N2 atmosphere. After cooled toroom temperature, the solution was diluted with 50 mL of EtOH and passedthorough celite and concentrated. Hexane/EtOAc (1/1) was added andextracted with water twice. To the aqueous layer, 1 M HCl was addeddropwise until the pH was approximately 2, and the resulting suspensionwas extracted twice with EtOAc. The combined organic layer was dried withNa2SO4 and passed through a short pad of silica-gel and concentrated in vacuo.To a suspension of the residue, K2CO3 (251 mg, 1.82 mmol) and Pd(PPh3)4(32 mg, 0.027 mmol) in degassed DME/H2O (9/1; 6 mL) under a N2atmosphere, bromobenzene (0.142 mL, 1.37 mmol) was added. After stirringat reflux for 6 h, the reaction solution was cooled to room temperature, dilutedwith EtOAc, and passed through celite. The filtrate was washed with water andbrine, dried with Na2SO4, and concentrated in vacuo. The residue was purifiedby silica gel column chromatography (hexane?hexane/diethylether = 98/2) togive 88 mg of 4-methyl-1,10:40,100-terphenyl (40% from 3 after 2 steps) as awhite powder. Mp: 205-207 C (lit.20a 206-208 C). The 1H and 13C NMRspectra corresponded to literature data

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 50670-49-0.

Reference:
Article; Kuno, Shinichi; Kimura, Tomoyuki; Yamaguchi, Masanori; Tetrahedron Letters; vol. 55; 3; (2014); p. 720 – 724;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 14922-91-9, name is 5-Bromo-2-ethylaniline, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

Step 2: Preparation of 4-bromo-1-ethyl-2-iodobenzeneTo a stirred mixture of 5-bromo-2-ethylaniline (3.39 g, 200 mmol) in distilled water (110 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.

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; SYNGENTA LIMITED; MATHEWS, Christopher, John; SCUTT, James, Nicholas; WO2011/6543; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, A new synthetic method of this compound is introduced below., Product Details of 142808-15-9

Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (5000 mL), NH(i-Pr)2 (249 g, 1.20 equiv). This was followed by the addition of n-BuLi (905 mL, 1.10 equiv) dropwise with stirring in 30 min at -70C. The resulting solution was stirred for 0.5 hr at -30C. To this was added 4-bromo-2-fluoro- l-(trifluoromethyl)benzene (500 g, 2.06 mol, 1.00 equiv) dropwise with stirring at -78C in 2 hr. The resulting solution was stirred for 2 hr at -78C. The reaction was then poured into 1000 g of C02(s) at -70C. The pH value of the solution was adjusted to 3 with hydrogen chloride (2N) (1.5 mol/L). The resulting solution was extracted with 3×2000 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 301 g (50%) of 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid as a white solid.

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 34950-82-8, 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 34950-82-8 as follows.

To a solution of I-69 (300 mg, 0.6 mmol) in DMF (10 mL) are added I-87 (140 mg, 0.7 mmol), tetrakis(triphenylphosphine)palladium (0) (70 mg, 0.06 mmol) and 2M Na2CO3 (1.5 mL, 3.0 mmol). The mixture is heated to 100 C. for 1 hour in a microwave reactor. The mixture is cooled down and is extracted with H2O (20 mL) and EtOAc (30 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (200 mg). Example 176-180, Table 1-the reaction is run at 120 C.Example 176-180, Table 1-the reaction is run at 120 C. [0509] Example 184-185, Table 1-the reaction is run at 120 C Example 191, Table 1-the reaction is run at 120 C. Example 239-243, Table 1-the reaction is run for 6 hours at 100 C. in an oil bath

According to the analysis of related databases, 34950-82-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 15155-41-6, 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 15155-41-6 as follows.

Synthesis of 3,6-dibromobenzene-1,2-diamine: Dibromobenzo[c][1,2,5]thiadiazole (2.29 g, 10 mmol) and sodiumborohydride (5.7 g, 150 mmol) were added to ethanol at 0 Cand stirred at room temperature for 36 h. The solution wasadded water and ethyl acetate then was separated by separatoryfunnel. The organic layer was dried over MgSO4 then concentrated under reduced pressure and purified by chromatographyon a silica column eluting with petroleum ether/ethyl acetate(5:1, v/v) to afford a yellow solid (1.9 g, 71 % yield). 1H NMR(400 MHz, CDCl3, ppm) delta-aromatic H, 6.86 (d, 2H), 3.92 (s,4H); 13C NMR (100 MHz, CDCl3, ppm): 133.73,123.27, 109.70.

According to the analysis of related databases, 15155-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sun, Xiaoxia; Lei, Xiaolong; Hu, Yu; Asian Journal of Chemistry; vol. 27; 7; (2015); p. 2427 – 2430;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 22385-77-9, These common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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 solution of2,2,6,6-tetramethylpiperidine (1.6 mL, 9.6 mmol) in THF (10 mL) was treated withn-BuLi (6.0 mL, 1.60 M in hexane, 9.6 mmol) at 0 ¡ãC. After stirring for 1 h at 0 C thesolution was added to a solution of compound 3 (1.81 g, 4.00 mmol) in THF (8 mL) at?78 ¡ãC. After stirring for 30 min at ?78 ¡ãC and 3 h at ?30 ¡ãC the reaction mixture wastransferred to a suspension of ZnCl2 (1.09 g, 8.00 mmol) in THF (8 mL) at ?78 ¡ãC.Stirring was continued at ?78 ¡ãC for 30 min before the mixture was warmed to roomtemperature, where stirring was maintained for 30 min. To the resulting solution wasadded a solution of 1-bromo-3,5-di-t-butylbenzene (1.18 g, 4.40 mmol) and [Pd(PPh3)4](0.23 g, 0.20 mmol) in THF (8 mL). The reaction mixture was heated to 60 ¡ãC for 10hours, before the reaction was quenched with a saturated aqueous ammonium chloride solution. The reaction mixture was extracted with hexane and the combined organicphases were washed with water and dried over MgSO4. After filtration, the filtrate wasevaporated to dryness under reduced pressure and the obtained residue was purified bycolumn chromatography on silica gel (hexane). Washing the resulting solid with smallamount of methanol to give compound 4 (1.99 g, 3.10 mmol, 78percent). 4: orange solid, m.p.139-141 ¡ãC. 1H NMR (300 MHz, CDCl3) delta 1.39 (s, 36H), 4.14 (s, 5H), 4.59 (s, 2H),7.35 (t, J = 1.8 Hz, 1H), 7.62 (d, J = 1.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) delta 31.5 (q),34.9 (s), 67.0 (d), 73.5 (d), 79.7 (s), 88.6 (s), 120.9 (d), 124.4 (d), 135.5 (s), 149.8 (s).Anal. Calcd for C38H49BrFe: C, 71.14; H, 7.70percent. Found: C, 71.30; H, 7.66percent.

The synthetic route of 22385-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sasamori, Takahiro; Suzuki, Yuko; Sakagami, Michiyasu; Miyake, Hideaki; Tokitoh, Norihiro; Chemistry Letters; vol. 43; 9; (2014); p. 1464 – 1466;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 22034-13-5, 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 22034-13-5 as follows.

A mixture of (9,9-di-n-hexyl-9H-fluoren-2-yl)boronic acid [J. Am. Chem. Soc, 2004, 126, 13695-13702] (915 mg, 2.42 mmol), 4-bromobenzo[c] [l,2,5]thiadiazole [J. Phys. Chem. B, 2012, 116, 7259-7268] (434 mg, 2.02 mmol), and potassium carbonate (1.20 g, 8.70 mmol) in toluene (20 mL), ethanol (8 mL), and water (12 mL) was placed under vacuum until boiling and backfilled with argon six times. Tetrakis(triphenylphosphine)- palladium(O) (100 mg, 0.087 mmol) was added and the solution heated in an oil bath held at 100¡ãC overnight under a blanket of argon. The solution when then cooled, diluted with water (90 mL), diethyl ether (90 mL), brine (60 mL), and the layers separated. The aqueous solution was extracted with diethyl ether (3 x 60 mL) and the combined organic extracts were washed with water (2 x 60 mL), brine (60 mL), dried over anhydrous magnesium sulphate, filtered on a silica plug, and the solvent removed in vacuo. The crude residue was purified by column chromatography over silica using a dichloromethane: light petroleum mixture (0: 1 to 1 : 10) as eluent to afford AL03-77 as yellow/green oil after removal of the solvent (751 mg, 79percent). 1H NMR (500 MHz, CDC13) delta: 0.66-0.83 (10H, m, HexH), 1.00- 1.12 (12H, m, HexH), 1.95-2.09 (4H, m, HexH), 7.31- 7.40 (3H, m, FIH), 7.71 (1H, dd, = 8.5, 8.5 Hz, BTH), 7.76 (2H, dd, = 1.0, 7.0 Hz, FIH), 7.85 (1H, dd, = 0.5, 8.0 Hz, BTH), .90 (1H, d, = 0.5 Hz, BTH), 7.97 (1H, dd, = 1.5, 8.0 Hz, FIH), 8.00 (1H, dd, = 1.0, 8.5 Hz, FIH). HRMS (ESI-MS) for C31H36N2S [M + Na]+ Calcd: 491.2491 (100percent), 492.2522 (34percent), 493.2511 (10percent). Found: 491.2491 (100percent), 492.2500 (40percent), 493.2480 (12percent).

According to the analysis of related databases, 22034-13-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF QUEENSLAND; BURN, Paul Leslie; SHAW, Paul Edward; (64 pag.)WO2019/79860; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary