Category: 452-92-6

Adding a certain compound to certain chemical reactions, such as: 452-92-6, name is 5-Bromo-2,4-difluoroaniline, 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 452-92-6, COA of Formula: C6H4BrF2N

General Procedure: Methyl 2-{[4-(chlorosulfonyl)-2,3-dimethylphenyl]oxy}propanoate (7) (4 g, 13.0 mmol) was dissolved in pyridine (10 mL). After 5 min, 3-bromo-2-chloroaniline (3.22 g, 15.6 mmol) was added. The reaction was complete within a few hours. The reaction mixture was then extracted using diethyl ether. The combined organic phases were washed with 1N HCl and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2,4-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Article; Evans, Karen A.; Shearer, Barry G.; Wisnoski, David D.; Shi, Dongchuan; Sparks, Steven M.; Sternbach, Daniel D.; Winegar, Deborah A.; Billin, Andrew N.; Britt, Christy; Way, James M.; Epperly, Andrea H.; Leesnitzer, Lisa M.; Merrihew, Raymond V.; Xu, Robert X.; Lambert, Millard H.; Jin, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 8; (2011); p. 2345 – 2350;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 452-92-6,Some common heterocyclic compound, 452-92-6, name is 5-Bromo-2,4-difluoroaniline, molecular formula is C6H4BrF2N, 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 a solution of 5-bromo-2,4-difluoro-aniline (1.0 g, 4.81 mmol) in acetone (25.0 mL) was added drop wise benzoyl isothiocyanate (0.71 mL, 5.29 mmol) and the mixture stirred at RT for 30 min. The solvent was evaporated and the residue washed with hexane and Et2O to get i(1.70 g). 1H-NMR (400 MHz, CDCl3): delta 7.02-7.06 (m, 1H), 7.56 (t, J=8.0 Hz, 2H), 7.68 (t, J=7.60 Hz, 1H), 7.91 (d, J=7.60 Hz, 2H), 8.67 (t, J=7.60 Hz, 1H), 9.15 (br s, 1H) and 12.65 (br s, 1H).

The synthetic route of 452-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biota Europe Ltd.; Lunniss, Christopher James; Palmer, James T.; Pitt, Gary Robert William; Davies, David; Axford, Lorraine Claire; US2013/252938; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 452-92-6, name is 5-Bromo-2,4-difluoroaniline, 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 452-92-6, category: bromides-buliding-blocks

Potassium o-ethyl carbondithioate (5.36 g, 33.5 mmol), 5-bromo-2,4- difluoroaniline (5.8 g, 27.9 mmol) were combined in dry N-methyl-2-pyrrolidone (NMP; 40 mL) and heated to 100C for 18 h. After cooling, the mixture was partitioned between EtOAc (50 mL) and water (30 mL). The aqueous, phase was extracted with EtOAc (30 mL) and the combined organic phases were washed water (2 x 25 mL), satd NaCl (25 mL), dried and concentrated to give the intermediate thiol (5.4 g) as a tan solid. This material was combined in methanol (120 mL) with nickel chloride hexahydrate (3.3 g, 14 mmol)and zinc powder (3.7 g, 56 mmol), heated to reflux and treated dropwise with concentrated HC1 (20 mL). The reaction mixture was heated for 2 h after the addition was complete. The cooled mixture was stirred with EtOAc (200 mL) and treated with concentrated aq ammonia until the pH was > 10. The organic phase was washed with satd NaCl (40 mL), dried and concentrated. Purification by chromatography with 0-40% EtOAc-hexanes gave the title compound as a yellow solid (3.2 g, 47%): mp 86-88 C; NMR (400 MHz, DMSO-d6) delta 9.44 (s, 1H), 8.47 (d, / = 6.3 Hz, 1H), 8.30 (d, J = 8.6 Hz, 1H); 19F NMR (376 MHz, DMSO-d6) delta -111.18; EIMS m/z 232.

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; DOW AGROSCIENCES LLC; BELL, Jared; BUYSSE, Ann M.; DAEUBLE, John F.; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; IRVINE, Nicholas M.; KISTER, Jeremy; LO, William C.; LOSO, Michael R.; LOWE, Christian T.; ROHANNA, John C.; SATCHIVI, Norbert M.; SIDDALL, Thomas L.; STEWARD, Kimberly M.; YERKES, Carla N.; (281 pag.)WO2019/84353; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

452-92-6, Name is 5-Bromo-2,4-difluoroaniline, 452-92-6, 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.

A solution of 2,4-difluoro-6-bromoaniline (5 g, 24 mmol), salicylaldehyde (2.5 mL, 24 mmol) and p-toluenesulfonic acid (14 mg, 0.07 mmol) in toluene (120 mL) was heated to reflux in a Dean-Stark apparatus for 2.5 h and then allowed to cool to ambient temperature. After adding triethylamine (1 mL) the reaction mixture was concentrated to give the crude title compound (7.3 g, 97%) which was used without further purification. 1H-NMR (400 MHz, CDCl3) 6.95-6.99 (m, 1H), 7.01-7.06 (m, 2H), 7.39-7.45 (m, 2H), 7.48-7.52 (m, 1H), 8.66 (s, 1H), 12.69 (s, 1H). (m/z)=312+314 (M+H)+.

Statistics shows that 5-Bromo-2,4-difluoroaniline is playing an increasingly important role. we look forward to future research findings about 452-92-6.

Reference:
Patent; N.V. Organon; US2008/90804; (2008); 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 452-92-6 as follows. 452-92-6

To a solution of 5-bromo-2,4-difluoro aniline (1.0 g, 4.81 mmol) in acetone (25.0 ml.) was added drop wise benzoyl isothiocyanate (0.71 mL, 5.29 mmol). The resulting reaction mixture was allowed to stir at room temperature for 30 min. After the completion of the reaction (TLC monitoring), the solvent was evaporated and the residue was washed with hexane and ether to get the title compound (1.70 g, quantitative yield) as a white solid. 1H-NMR (400 MHz, CDCI3): delta 7.02-7.06 (m, 1 H), 7.56 (t, J= 8.0 Hz, 2H), 7.68 (t, J= 7.60 Hz, 1 H), 7.91 (d, J= 7.60 Hz, 2H), 8.67 (t, J= 7.60 Hz, 1 H), 9.15 (br s, 1 H) and 12.65 (br s, 1 H).

According to the analysis of related databases, 452-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROLYSIS LTD; WO2009/74812; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

452-92-6, 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 452-92-6 as follows.

5-bromo-2,4-difluoroaniline (500 mg, 2.40 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzoate (BSfTERMEDIATE 16, 797 mg, 2.88 mmol), sodium carbonate (2.40 mL, aq., 2M, 2.88 mrnol), l,l’-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (196 mg, 0.24 mmol) and ethanol (15 ml) were heated in an 80 0C oil bath for 3 hours then allowed to cool to ambient overnight. Volatiles were removed under reduced pressure. The pot residue was worked up w/DCM /brine/Na2Sthetayfltratio:n/concentration to afford a dark oil. The resulting oil was purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 40% EtOAc/hexa?es gradient mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc. = 277.09; found = 278.03 (M+l)+.; Step A methyl 5′-amino-2′,4′-difluoro-2-methylbiphenyl-4-carboxyIate5-bromo-2,4-difluoroaniline (500 mg, 2.40 mmol), methyl 3-methyl-4-(4,4,5,5-tetrarnethyl-l,3,2- dioxaborolan-2-yl)benzoate (INTERMEDIATE 16, 797 mg, 2.88 mmol), sodium carbonate (2.40 mL, aq., 2M, 2.88 mmol), l,r-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (196 mg, 0.24 mmol) and ethanol (15 ml) were heated in an 80 0C oil bath for 3 hours then allowed to cool to ambient overnight. Volatiles were removed under reduced pressure. The pot residue was worked up w/DCM /brine/Na2SCVfltration/concentration to afford a dark oil. The resulting oil was purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 40% EtOAc/hexanes gradient mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc. = 277.09; found = 278.03 (M+l)+.

According to the analysis of related databases, 5-Bromo-2,4-difluoroaniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary