Month: February 2021

These common heterocyclic compound, 1422-53-3, name is 2-Bromo-4-fluorotoluene, 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. COA of Formula: C7H6BrF

Reference Example 3 Production of 5-fluoro-2-methylbenzaldehyde: Iodine (about 1 mg) was added to a mixture of magnesium (26.28 g) and tetrahydrofuran (600 ml) and 2-bromo-4-fluorotoluene (200.4 g) was added dropwise thereto with ice-cooling (the inner temperature was kept at 65C or lower). After completion of the dropwise addition, the mixture was stirred for 1 hour to prepare a Grignard reagent.

The synthetic route of 2-Bromo-4-fluorotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1229019; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 67567-26-4, 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. 67567-26-4 name is 4-Bromo-2,6-difluoroaniline, 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.

A mixture of 4-bromo-2,6-difluoro-aniline (4.16 g, 20.0 mmol, 1.00 eq.) and ethoxycarbothioylsulfanyl potassium (7.69 g, 48.0 mmol, 2.40 eq.) in DMF (25 mL) was stirred at 130C overnight, then cooled to room temperature, diluted with 1 N HCl (150 mL) and stirred at room temperature for 1 h. The resulting solid was filtered and washed with water and dried. The resulting material was suspended in CH2Cl2 (25 mL) and SO2Cl2 (27.5 g, 16.5 mL, 200 mmol, 10.0 eq.) was added slowly and stirred at room temperature for 48 h. Water was added slowly at 0 C to quenched the reaction. The resulting precipitate was collected by filtration and purified over silica with ethyl acetate in hexanes (2 to 10% gradient) to give 6-bromo-2-chloro-4-fluoro- 1,3-benzothiazole (5.08 g, 95.3%). MS m/z 266.1, 268.0, 270.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); 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. 73790-19-9, name is 5-Bromo-2,2-dimethylbenzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Bromo-2,2-dimethylbenzo[d][1,3]dioxole

PREPARATION 158 2,2-Dimethyl-1,3-benzodioxol-5-ylboronic acid Obtained as a green solid (47%), m.p. 174-176 C., from 5-bromo-2,2-dimethyl-1,3-benzodioxole (GB-A-2187452) and trimethyl borate, using the procedure of Preparation 101. delta(DMSOd6): 1.60 (s,6H), 6.77 (d,1H), 7.17 (s,1H), 7.28 (d,1H), 7.80 (s,2H).

According to the analysis of related databases, 73790-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer INC; US6387931; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene, 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. Product Details of 18648-66-3

General procedure: A flask was charged with a mixture of 3-(4-vinylphenyl)-9-ethylcarbazole (1, 0.3 g, 1.01 mmol), 2-(4-bromophenyl)-1,1-diphenylethylene (triPE, 0.28 g, 0.84 mmol), palladium acetate(Pd(OAc)2, 2.3 mg, 0.01 mmol), P(o-tolyl)3 (15 mg, 0.05 mmol),dimethylformamide (8 mL) and trimethylamine (3 mL). The flaskwas degassed and purged with argon. The reaction mixture washeated at 90 C for 4 h under argon atmosphere. Then, it wasfiltered, and was purified by column chromatography using hexane/ethyl acetate (50/1) as an eluent. The target product wasrecrystallized from the eluent mixture of solvents. The yield ofyellow crystals was 43% (0.2 g).

The synthetic route of 18648-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tomkeviciene; Sutaite; Volyniuk; Kostiv; Simkus; Mimaite; Grazulevicius; Dyes and Pigments; vol. 140; (2017); p. 363 – 374;,
Bromide – Wikipedia,
bromide – Wiktionary

22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, 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. HPLC of Formula: C6H3BrN2S

To a flask equipped with a reflux device, 2.7 g (24.2 mmol) of t-butoxypotassium, 0.3 g (0.4 mmol) of a Pd catalyst (PEPPSI?-IPr), 70 mL of toluene, 4.3 g (20.2 mmol) of the compound (b), and 1.8 mL (22.2 mmol) of pyrrolidine were added, and it was refluxed at 120¡ã C. for three hours under a nitrogen atmosphere. After a reaction was finished, solids in a reaction solution were removed by filtration, the filtrate was condensed, and then refinement was performed by column chromatography using dichloromethane as a developing solution, to thereby obtain a compound (c2) (2.9 g, 14 mmol, yield: 70percent).

The synthetic route of 22034-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGC Inc.; MIYAKE, Noriaki; Okada, Satoshi; Irisawa, Jun; Konishi, Teppei; Matsuura, Keigo; US2018/346729; (2018); 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. 51554-93-9, name is 1-Bromo-4-octylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 51554-93-9

General Procedure W: Synthesis of an alpha-beta unsaturated ketoneAn organometalic reagent (1-3 equivalents, preferably 1.1 equivalents) is added to a solution of a beta-alkoxy enone in an organic solvent (preferably THF) at about -78 C-room temperature (preferably 0 0C). Following the addition the reaction mixture is allowed to warm to about room temperature. After Ih IN HCl is added until a pH of 1 is obtained. The reaction mixture is taken through an aqueous work-up and the crude product can be purified by chromatography.Exemplification of General Procedure W: Preparation of 3-(4-octylphenyl)cyclohex-2-enoneTo a suspension of magnesium (1.477 g, 60.8 mmol) in THF (56 mL) was added 1-bromo- 4-octylbenzene (15.00 g, 55.7 mmol). After stirring for about 6h the reaction mixture was added with filtering to a solution of 3-ethoxycyclohex-2-enone (7.10 g, 50.6 mmol) in THF (28.0 mL) at 0 0C. Following the addition the reaction mixture was allowed to warm to room temperature. After Ih IN HCl was added until a pH of 1 was obtained. The reaction mixture was diluted with Et2O and the organic layer was separated, washed with NaHCO3, and brine, dried with Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel (EtOAc/Hep) to provide 3-(4-octylphenyl)cyclohex-2 -enone (9.5 g, 33.4 mmol, 65.9 % yield) as a colorless oil.LCMS (Table 1, Method a) R1 = 4.53 min; m/z: 285 (M-H)-; IH NMR (400 MHz, DMSO- d6) 5 7.57 (d, 2H), 7.25 (d, 2H), 6.34 (s, IH), 2.76 (dd, 2H), 2.60 (dd, 2H), 2.40 (dd, 2H), 2.03 (dddd, 2H), 1.58-1.55 (m, 2H), 1.27-1.24 (m, 10H), 0.85 (t, 3H).

The synthetic route of 51554-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/79382; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 500 mL three-necked flask was charged with benzophenone (79.8 g, 0.438 mol), trimethyl orthoformate (69.6 g,0.656 mol), p-toluenesulfonic acid (3.4 g, 0.02 mol) and methanol300mL, open the stirring, heat to reflux, heat for 3 hours, cool down and dilute the solvent under reduced pressure, add the product obtained in the previous step (62.4g, 0.438mol) and 300mL of toluene, increase to 80-110 degrees for 3 hours, increase the temperature The solvent was distilled off under normal pressure until the disappearance of the starting material by GC. The temperature was lowered, and the solvent was concentrated under reduced pressure to give a crude product 136.2 g, dissolved in 1.2 L acetonitrile, transferred to a 2 L reaction flask, and tetrabutylammonium bromide (282.1 g, 0.875) was added. Mol), copper bromide (0.98g, 0.004mol), tert-butyl nitrite (54.1g, 0.525mol) was added dropwise at 0-10 C, stirred at room temperature for 6 hours, TLC controlled material was completely reacted, hydrogen peroxide was added dropwise Sodium (73.5 g, 0.875 mol) dissolved in 600 mL of water, followed by 3-bromo-4-fluoroaniline (124.7 g, 0.656 mol), heated to 50 C, stirred for 1 hour, TLC controlled raw material reaction was complete, cooling , joinThe mixture was combined with EtOAc (EtOAc m.The obtained crude product was recrystallized from ethyl acetate / n-hexane to afford 137.4 g.Yield 65.4%

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Jinlu Pharmaceutical Technology Co., Ltd.; Gao Feng; Zeng Sailan; Jiang Junqiang; Zhang Xingxing; (8 pag.)CN108003112; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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 40161-54-4 as follows. SDS of cas: 40161-54-4

To a mixture of 1-bromo-2-fluoro-4- (trifluoromethyl) benzene (5.0 g, 0.02 mol) in EtOH (10 mL) was added Pd (dppf) Cl2 (1.46 g, 0.2 mmol ) and AcONa (3.37 g, 0.041 mol) , and the resulting mixture was stirred at 80under an atmosphere of CO (50 psi) for 8 hours. The mixture was then filtrated and the filtrate was partitioned with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (eluting with PE:EA10:1) to give the title compound. 1H NMR (400MHz, CDCl3) delta: 8.04-8.08 (t, 1H, J7.6 Hz) , 7.49-7.47 (d, 1H, J8.0 Hz) , 7.43-7.40 (d, 1H, J10.4 Hz) , 4.44-4.40 (q, 2H, J7.2 Hz) , 1.43-1.38 (t, 3H, J7.2Hz) .

According to the analysis of related databases, 40161-54-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BIFTU, Tesfaye; BIJU, Purakkatle; COLLETTI, Steven L.; CUI, Mingxiang; HAGMANN, William K.; HU, Bin; JOSIEN, Hubert; KAR, Nam Fung; NAIR, Anilkumar; NARGUND, Ravi; SPERBECK, Donald M.; ZHU, Chen; WO2015/51725; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 1647-26-3 as follows. Recommanded Product: 1647-26-3

EXAMPLE 8 5-[N-(2-cyclohexyl)-ethyl]-amino-2-(3,5-diethoxyphenyl)-2-isopropylvaleronitrile 30.4 g (0.1 mole) of 5-amino-2-(3,5-diethoxyphenyl)-2-isopropylvaleronitrile and 19.1 g (0.1 mole) of 2-bromoethylcyclohexane gave, after chromatographic purification of the product, 25.7 g (62%) of the base, the procedure used being similar to that described in Example 5.

According to the analysis of related databases, 1647-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US4940780; (1990); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1422-54-4, name is 2-Bromo-6-fluorotoluene, 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 1422-54-4, HPLC of Formula: C7H6BrF

Sodium benzyloxide was prepared by adding benzyl alcohol (20 mmol) to a suspension of NaH (20 mmol) in N-methylpyrrolidone . The freshly prepared solution (10.8 mmol) was added to 1- bromo-3-fluoro-2-methylbenzene (5.41 mmol) in N methylpyrrolidone . The reaction was heated at 100 C and was monitored by TLC until complete consumption of the starting material. Water and ethyl acetate were added, the aqueous layer was separated and the organic layer was washed with water, dried over MgS04, filtered and concentrated. The residue was chromatographed with hexane/EtOAc mixture. Yield: 92%. 1H NMR (500 MHz, CDC13) delta 7.49-7.39 (m, 4H) , 7.37 (d, J = 7.0 Hz, 1H) , 7.20 (d, J = 8.0 Hz, 1H) , 7.02 (t, J = 8.1 Hz, 1H) , 6.86 (d, J = 8.2 Hz, 1H) , 5.09 (s, 2H) , 2.41 (d, J = 3.3 Hz, 3H) . 13C NMR (126 MHz, CDC13) delta 157.5, 137.0, 128.6, 128.0, 127.3, 127.3, 127.2, 126.0, 125.0, 110.7, 70.5, 16.0. MS (EI) m/z 277 (M+) .

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; RIJKSUNIVERSITEIT GRONINGEN; DOeMLING, Alexander; (85 pag.)WO2017/118762; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary