Category: 1003-98-1

Application of 1003-98-1,Some common heterocyclic compound, 1003-98-1, name is 2-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.

To an ice-cooled mixture of 2-bromo-4-fluoroaniline (25.0 g, 0.132 mol), ammonium thiocyanate (40.0 g, 0.525 mol) in acetic acid (180 mL) was added dropwise a solution of bromine (13.5 mL, 0.264 mol) in acetic acid (35 mL) over 1 h. After stirring at room temperature for 2 h, the yellow insoluble material was collected by filtration. The yellow cake was suspended in water, and the pH was adjusted to 11 by adding potassium carbonate. The insoluble material was collected again, and the cake was purified by flash column chromatography on silica gel (Hexane:AcOEt = 3:1) to give the title compound as a yellow solid (29.7 g, 91%). Mp 183-185 C. 1H NMR (400 MHz, DMSO-d6) delta 7.37 (1H, dd, J = 8.5, 2.4 Hz), 7.64 (2H, dd, J = 8.5, 2.4 Hz), 7.82 (2H, brs). 13C NMR (100 MHz, DMSO-d6) delta 107.5 (d, J = 27.8 Hz), 109.4 (d, J = 11.5 Hz), 116.0 (d, J = 26.8 Hz), 131.8 (d, J = 11.5 Hz), 147.7 (d, J = 1.9 Hz), 156.2 (d, J = 239.6 Hz), 166.8. IR (ATR) nmax 3079, 1634, 1539, 1452, 1394, 1319, 1208, 1099, 1057, 940, 847 cm-1. MS (EI) 246 (M+). HRMS (EI) calcd for C7H4BrFN2S (M+) 245.9304, found 245.9263.

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Watanabe, Daisuke; Kohno, Yasushi; Seto, Shigeki; Tetrahedron; vol. 72; 12; (2016); p. 1566 – 1572;,
Bromide – Wikipedia,
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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. 1003-98-1, name is 2-Bromo-4-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromo-4-fluoroaniline

Example 100:; To a DMF solution (7ml_) of 4-fluoro-2-bromoaniline (258mg, 1.36mmol) was added the alkyne 92a (400mg, 1.36mmol), Pd(PPh3)2CI2 (38mg, 0.054mmol), CuI (20.6mg, O.H mmol) and i- Pr2NH (2 mL). The mixture was degassed in vacuo, flushed with nitrogen and heated at 90C for 1 h. The resulted solution was diluted with EtOAc (3OmL), washed with brine (2x25mL), dried (MgSO4) and concentrated in vacuo. The residue was purified with silica gel column chromatography (15% EtOAc in hexanes) giving the title compound (320mg, 58% yield) as a solid. ). LCMS (APCI positive): 405 (M+H+).

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER, INC.; WO2006/40646; (2006); 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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5BrFN

Example (III-1) Preparation of Starting Materials of the Formula (III) Under an atmosphere of inert gas (argon), 4.5 ml of a saturated sodium carbonate solution and 0.1 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium(0) are added to a suspension consisting of 0.9 g (4.8 mmol) of 2-bromo-4-fluoroaniline and 1.0 g (5.1 mmol) of [3-fluoro-4-(methoxycarbonyl)phenyl]-boronic acid in 5 ml of toluene and 0.5 ml of ethanol. The reaction mixture is stirred at 80 C. for 16 hours and then poured into 10 ml of water and extracted with 20 ml of toluene. The combined organic phases are dried over magnesium sulphate, filtered and concentrated under reduced pressure. Column chromatography (gradient cyclohexane/ethyl acetate) gives 0.5 g (1.76 mmol, 37% of theory) of methyl 2′-amino-3,5′-difluorobiphenyl-4-carboxylate [log P (pH 2.3) 2.73].

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience AG; US2009/76113; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-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. Safety of 2-Bromo-4-fluoroaniline

The title compound was prepared by a modified procedure reported in the literature (Org. Lett., 2014, 16, 2916-2919). A mixture of 2-bromo-4-fluoroaniline (20 g, 105 mmol), PdCl2(PPh3)2 (7.39 g, 10.53 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (40.4 g, 316 mmol) and Et3N (58.7 mL, 421 mmol) in dioxane (400 mL) was stirred at 110C for 16 h under nitrogen atmosphere. It was cooled to rt and poured into a saturated aqueous solution of ammonium chloride (300 mL). The mixture was extracted with DCM (300 mL). The organic layer was separated, dried over sodium sulfate, and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel (eluting with EtOAc/petroleum ether = 10: 90 v/v) to give the title compound.1H NMR (400 MHz, CDCl3): delta 7.25 (m, 1H), 6.92 (m, 1H), 6.54 (m, 1H), 4.42 (brs, 2H), 1.34 (s, 12H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1003-98-1, These common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-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.

Example 148:; 148 EPO To a N, N-dimethyl-formamide solution (10 mL) of ethyl (3R)-3-[(tert-butoxycarbonyl)amino]hex-5- ynoate (1.26 g, 4.94 mmol) was added 4-fluoro-2-iodoaniline (1.29 g, 5.44 mmol), diisopropylamine (15 mL), dichlorobis(triphenylphosphine)-palladium (II) (76 mg, 0.109 mmol) and CuI (31 mg, 0.163 mmol). The mixture was stirred at 25C for 15h after three circles of nitrogen/vacuum flush. DMF was removed by vacuum and the residue was diluted with EtOAc (75 mL). It was then washed with NH4CI solution (1×50 mL) and brine (2×50 mL), dried with Na2SO4 and concentrated. After column chromatography (12% ethyl acetate in hexane), the title compound was obtained in 88% yield (1.58g). 1H NMR (CDCI3): delta 6.95 (1 H, m), 6.84 (1 H, m), 6.64 (1 H, m), 5.26 (1 H, br s), 4.22-4.10 (3H, m), 2.82-2.60 (4H, m), 1.44 (9H, s), 1.27 (3H, t, J=7.1 Hz).

Statistics shows that 2-Bromo-4-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 1003-98-1.

Reference:
Patent; PFIZER, INC.; WO2006/40646; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-98-1, 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. 1003-98-1 name is 2-Bromo-4-fluoroaniline, 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.

2-Propyl-3-propyl-5-fluoro-1H-indole; A 50 mL three neck flask was charged with palladium acetate (22.4 mg, 0.1 mmol), dtbpf (94 mg, 0.2 mmol), potassium carbonate (690 mg, 5 mmol), 2-bromo-4-fluoroaniline (380 mg, 2 mmol), 4-octyne (264 mg, 2.4 mmol) and NMP (10 ml). The mixture was purged with argon and heated to 130 C. After 1 hr, the reaction mixture was cooled to rt. Ethyl acetate and water were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine and dried with MgSO4. Removal of the solvents and purification of the crude by column chromatography afforded the desired product as yellow oil (355 mg, containing 4.3 wt % AcOEt). The corrected yield was 77.6%. 1H NMR (400 MHz): delta=7.68 (s, 1H), 7.16-7.13 (m, 2H), 6.83 (td, 1H, J=9.2 Hz, J=2.4), 2.68 (t, 2H, J=7.6 Hz), 2.61 (t, 2H, J=7.6), 1.72-1.57 (m, 4H), 0.98 (t, 3H, J=7.2 Hz), 0.95 (t, 3H, J=7.2 Hz).

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; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-98-1, 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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 5 2-(2-amino-5-fluorophenyl)-3-methyl-2-cyclopenten-1-one 4.46 g (21.44 mmol) of 2-bromo-4-fluoroaniline, 3.30 g (23.582 mmol) of 5-methyl-1-cyclopenten-2-one boronic acid compound, 0.204 g (0.177 mmol) of tetrakis(triphenylphosphine)palladium, and 3.41 g (32.173 mmol) of sodium carbonate were loaded to 250 mL schlenk flask, and then 66 mL of degassing DME and 22 mL of H2O that had been purged with N2 were added thereto using a syringe. The mixture was reacted at 90 C. for 12 hours. The work-up was the same as in Example 3 (3.76 g, 79%). 1H NMR (CDCl3): =6.74(td, J=8.8 Hz, 1H, Ph), 6.45 (d, J=7.6 Hz, 1H, Ph), 3.65 (br s, 2H, NH2), 2.71-2.69 (m, 2H, CH2Cp), 2.54-2.52 (m, 2H, CH2CP), 2.07 (s, 3H, CH3); 13C {1H} NMR (CDCl3): =207.05, 176.05, 155.17(d, J=12.9 Hz, Ph), 152.63 (dd, J=12.9 Hz, Ph), 150.11 (d, J=12.9 Hz, Ph), 137.79, 129.60(d, J=3.1 Hz, Ph), 120.43 (dd, J=12.9 Hz, Ph), 111.97 (dd, 1.8 Hz, 22 Hz, Ph), 103.00 (t, 22 Hz, Ph), 34.66, 32.28, 18.50

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; LG Chem, Ltd.; US7538239; (2009); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-98-1,Some common heterocyclic compound, 1003-98-1, name is 2-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.

Compound 15 (67.5 g, 0.355 mol) was added to the 300 mL 15 % aq. HCl. A resulting suspension was stirred for 1 h at 80 oC, then cooled to -5 C and NaNO2 (26.0 g, 0.365 mol) in H2O (50 mL) was slowly added. The mixture was stirred for 1.5 h at -5 C and then the excess of HNO2 was neutralized with urea. The solution of KI (57.2 g, 0.0355 mol) in 50 mL H2O was added dropwise at 0 oC (caution, the fast evolution of N2 was observed). The mixture was warmed to room temperature and stirred for 40 h. After this time CHCl3 was added, water phase was extracted with CHCl3 (3 ¡Á 100 mL), joined organic phases were washed with saturated solution of NaHCO3 (200 mL), 5% solution of Na2S2O3 (200mL) and5% solution of Na2S2O5 (200mL). Organic phase was dried over MgSO4 and concentrated under reduced pressure. The obtained crude product was distilled under reduced pressure (b.p. 90-91 oC, 2 Tr) affording 17 as viscous oil (69.1 g, 64%). 1H NMR (400 MHz, CDCl3): delta 7.79 (ddd, J = 9.0, 5.8, 0.9 Hz, 1H), 7.38 (ddd, J = 8.3, 2.9, 0.8 Hz, 1H), 6.78 (ddd, J = 9.0, 7.9, 2.9 Hz, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-98-1, its application will become more common.

Reference:
Article; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1003-98-1 name is 2-Bromo-4-fluoroaniline, 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. 1003-98-1

General procedure: 4.2 General procedures: A. Microwave. Neat samples of amine (1.00 mmol) and carboxylic derivative (methyl ester or acid, 1.00 mmol) and DABAL-Me3 (202 mg, 0.8 equiv) were placed in a 5 mL microwave vial and dry THF added (1 mL) under a blanket of argon. For coupling partners containing acidic hydrogens additional DABAL-Me3 (total of 410 mg, 1.6 equiv) was used. The vial was promptly capped and placed in a CEM Discover microwave reactor. After irradiation (290 W, 130 C, 8 min) and programmed cool down (ca. 20 min). The reactions were quenched by cautious addition of HCl (2 M, 4 mL) or aqueous solutions of Rochelle salt (saturated potassium sodium tartrate, 4 mL) (CARE: methane liberated). Extraction with dichloromethane, drying (MgSO4) and evaporation frequently provided the pure products directly. If purification was required column chromatography 3:2 to 2:3 hexane:EtOAc was used for amides lacking highly polar functional groups (CH2Cl2 with 2 % v/v MeOH was used for amides bearing pendant amines, alcohols and other polar functional groups).

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

Reference:
Article; Dubois, Nathalie; Glynn, Daniel; McInally, Thomas; Rhodes, Barrie; Woodward, Simon; Irvine, Derek J.; Dodds, Chris; Tetrahedron; vol. 69; 46; (2013); p. 9890 – 9897;,
Bromide – Wikipedia,
bromide – Wiktionary