Category: 65896-11-9

Synthetic Route of 65896-11-9, These common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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.

Stage 1: N-[1-(2-Bromo-6-fluorophenyl)-1H-1,2,4-triazol-3-yl]benzamide Ethyl [5-phenyl-1,2,4-oxadiazol-3-yl]imidoformate (2.00 g) and 2-bromo-6-fluoroaniline were heated to 150 C. for 4 h, the reaction mixture was cooled down to room temperature, the residue was stirred with 20 ml of ethanol for 45 minutes and the remaining solids were filtered off with suction. This left 2.0 g of the desired title compound. HPLC-MS: log P (neutral)=1.79; mass (m/z): 361 (M+H)+; 1H NMR (DMSO-D6) 7.587 (m, 2H), 7.638 (m, 3H), 7.768 (m, 1H), 8.002 (m, 2H), 8.891 (s, 1H), 11.053 (s, 1H).

Statistics shows that 2-Bromo-6-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 65896-11-9.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; HEILMANN, Eike Kevin; WROBLOWSKY, Heinz-Juergen; TRAUTWEIN, Axel; GREUL, Joerg; DEMBSKI, Hardwin; ILG, Kerstin; PORTZ, Daniela; GOERGENS, Ulrich; (85 pag.)US2017/73318; (2017); 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 65896-11-9 as follows. Computed Properties of C6H5BrFN

2-Bromo-6-fluoroaniline (2.0 g, 10 mmol) was dissolved in hydrochloric acid (7.0 niL, 12 N aqueous, 8.0 eq?iv) and cooled to 0 0C. An aqueous solution (10 mL) of sodium nitrite (0.80 g, 11 mmol, 1.1 equiv) was added dropwise over 30 minutes via addition funnel and the mixture was stirred for an additional 30 minutes at 0 0C. A hydrochloric acid solution (10 mL, 12 N aqueous) of stannous chloride (7.1 g, 31 mmol, 3.0 equiv) was then added to the mixture over 45 minutes via addition funnel and the mixture was stirred for an additional 1 hour at 0 0C. To the mixture, sodium hydroxide (30 mL, 1 N aqueous) was added slowly until basic (p? >; 8). The mixture was warmed to ambient temperature, poured into sodium hydroxide (50 mL, 25% aqueous) and the aqueous layer was extracted with diethyl ether (3 X 250 mL). The combined organic extracts were dried with sodium sulfate, filtered and partially concentrated in vacuo. The mixture was diluted with diethyl ether (200 mL) and treated with gaseous hydrochloric acid until saturated, resulting in a white precipitate, which was filtered and washed with diethyl ether (2 X 50 mL), providing the titled compound as a white solid.

According to the analysis of related databases, 65896-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2010/96338; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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 65896-11-9, SDS of cas: 65896-11-9

2-Bromo-6-fluoroaniline (8.2 g, 43.2 mmol) was dissolved in pyridine (10 mL) and treated with pivaloyl chloride (7.0 mL, 57.2 mmol). The reaction was stirred at room temperature for 3 h. The reaction mixture was concentrated in vacuo and treated with ethyl acetate (50 mL). Mixture was washed 1 N hydrochloric acid (2¡Á), then brine. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was triturated with hexanes to give a solid which was filtered, washed with hexanes, and dried in vacuo. The title compound was obtained as white solid in 76% yield. 1H NMR (300 MHz, CDCl3): delta 7.39-7.31 (m, 1H), 7.14-7.03 (m, 2H), 6.98 (bs, 1H), 1.34 (s, 9H). Mass spec.: 274.1 (MH)+, 276.1 (MNa)+.

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; Degnan, Andrew P.; Han, Xiaojun; Dubowchik, Gene M.; Macor, John E.; Mercer, Stephen E.; US2005/215576; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 65896-11-9,Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-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.

Example 2A Methyl (2E)-3-[2-amino-3-fluorophenyl]propenoate Starting with 42.00 g (221.04 mmol) of 2-bromo-6-fluoroaniline, the general procedure [B] gives 29.66 g (68% of theory) of product. HPLC (method 1): Rt=4.14 min MS (ESIpos): m/z=196 (M+H)+

The synthetic route of 65896-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer HealthCare AG; US2007/185121; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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 65896-11-9, SDS of cas: 65896-11-9

General procedure: D.7. Synthesis of com ounds 126 to 131. 126 to 131 To a solution of anilines (0.12 mmol) in THF (800 mu) at 0 C, was added triphosgene (21 mg, 0.07 mmol). The mixture is stirred at rt for 1 h30, then TEA (70 mu, 0.50 mmol), (1 S)-1-methyl-1 ,2,3,4-tetrahydroisoquinoline hydrobromide (commercial, 27 mg, 0.12 mmol). The mixture was stirred at rt for 1 h, then overnight at 60 C. The reaction mixture is diluted with EtOAc (2 mL), then washed with an aqueous saturated solution of NaHC03. The organic layer was dried over MgS04, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (basic mode, LCMS prep). compounds 126, 127, 128, 129, 130 and 131 were synthesized following this method. (1 S)-N-(2-bromo-6-fluorophenyl)-1-methyl-3,4-dihvdroisoguinoline-2(1 H)-carboxamide 126. Compound 126 was prepared using 2-bromo-6-fluoroaniline as starting material Yield: 52%. LCMS (ES+): 363 (M+H)+, 96.9% purity.

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; UCB BIOPHARMA SPRL; VALADE, Anne; JNOFF, Eric; ATES, Ali; BURSSENS, Pierre; SKOLC, David; (211 pag.)WO2016/55479; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-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. 65896-11-9

General procedure: To a solution of o-haloaniline (4.63 mmol) in dry DCM (20 mL) at room temperature was dropped acyl chloride (5.09 mmol). The reaction mixture was stirred for 24 hours then poured into water, extracted with DCM, washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The product was carried on to next step without any further purification in most cases.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65896-11-9, its application will become more common.

Reference:
Article; Shi, Yajie; Zhou, Qifan; Du, Fangyu; Fu, Yang; Du, Yang; Fang, Ting; Chen, Guoliang; Tetrahedron Letters; vol. 60; 40; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

65896-11-9, 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 65896-11-9 as follows.

To a suspension of sodium perborate tetrahydrate (135.374 g., 886.4 mmol) in 500 mL acetic acid at 55 C. was added dropwise a solution of 2-bromo-6-fluoro-phenylamine (33.685 g., 177.271 mmol) in 70 mL acetic acid over 1 hour. The reaction mixture was stirred at 55 C. for an additional 3 hours, then cooled to 0 C. in an ice bath. Insoluble materials were removed by filtration through a plug of celite, which was rinsed with 100 mL acetic acid. The combined acetic acid fractions were added to 3 L ice water with stirring to give a waxy solid which was removed by filtration. The crude solid was dissolved in 250 mL ethyl acetate, washed three times with 200 mL of 10% aqueous hydrogen chloride, 200 mL saturated sodium bicarbonate and 100 mL brine. The solution was concentrated in vacuo to give 11.51 g of 1-bromo-3-fluoro-2-nitro-benzene as a red oil, 1H NMR (CDCl3, 300 MHz) delta: 7.26 (m, 1H), 7.38 (m, 1H), 7.49 (m, 1H)

According to the analysis of related databases, 65896-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2007/15744; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary