Category: 1003-99-2

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-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 1003-99-2, category: bromides-buliding-blocks

General procedure: In the MW method, a mixture of 4-chloro-5,6,7-trimethoxyquinazoline (3.0 mmol) and aryl amine (3.0 mmol) in 2-propanol (10 mL) was stirred for 3 min and then reacted under MW at 100 W and 80 ¡ãC for 20 min. Upon reaction completion as monitored by thin-layer chromatography (TLC), the solvent was removed under reduced pressure. The residue was dissolved with methanol or chloroform and purified by TLC (petroleum ether/ethylacetate, 1:2, V:V). The target compound was eluted from the silica gel with ethyl acetate to give the title compounds.

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Reference:
Article; Zhang, Ying; Jin, Linhong; Xiang, Hongmei; Wu, Jian; Wang, Peiyi; Hu, Deyu; Xue, Wei; Yang, Song; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 335 – 344;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1003-99-2, 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1; Synthesis of l-ethyl-3-[4-fluoro-7-(3-fluoropyridin-2-yl)-5-(pyridin-3-yl)-l,3- benzothiazol-2-yl]urea (Compound No. 1); Step 1 : Synthesis of N-(2-bromo-5-fluorophenyl)-2,2-dimethylpropanamide :; To a solution of 2-bromo-5-fluoroaniline (15.0 g, 85.7 mmol) in dichloromethane (120 mL) were added triethylamine (11.25 g, 110.0 mmol) followed by pivaloyl chloride (11.3 g, 92.0 mmol) drop-wise at 0 0C and then stirred at 25-30 0C for about 4 hours. The reaction mixture was diluted with dichloromethane and washed with saturated solution of sodium bicarbonate followed by water. The organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated to give the crude residue, which was purified through column chromatography using silica gel 230-400 mesh size and eluted with 5percent ethyl acetate in hexane to yield the title compound (20 g)

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2009/156966; (2009); 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, A new synthetic method of this compound is introduced below., COA of Formula: C6H5BrFN

3-methyl-4-nitrobenzoyl chloride (5.496g, 27.62 mmol) dissolved in 2 mL of dry pyridine was added to a stirringsolution of 2-bromo-5-fluoroaniline (5.248 g, 27.62 mmol) in dry pyridine (10mL). The dark brown solution was heated under reflux for 2 hours, then pouredinto water (30 mL), forming a precipitate that was collected and washed withwater and methanol, to afford a white solid (8.128 g, 84percent yield). 1HNMR (400 MHz, DMSO-d6): 10.38 (bs, 1H, NH-CO)delta, 8.13 (d, J=8.6 Hz, 1H, H-5?), 8.07 (bs, 1H, H-2?), 8.00 (dd, J=2.3, 8.7 Hz, 1H, H-6?), 7.78 (dd, J=5.8, 9.0 Hz, 1H, H-3), 7.53 (dd, J= 3.2, 9.9 Hz, 1H, H-6), 7.18 (td, J=8.7 Hz, 3.32, 1H, H-4), 2.59 (s, 3H,CH3); 13C NMR (100 MHz, DMSO-d6): delta 164.43,162.78, 160.35, 151.29, 138.04, 134.35, 133.36, 132.57, 127.07, 125.10, 116.32,116.08, 115.70, 19.80. MS: m/z (HRMS)calcd. for C14H11BrFN2O3+352.9932, 354.9912 [M+H], MS found: 354.9938 [M+H].

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:
Article; Stone, Erica L.; Citossi, Francesca; Singh, Rajinder; Kaur, Balvinder; Gaskell, Margaret; Farmer, Peter B.; Monks, Anne; Hose, Curtis; Stevens, Malcolm F.G.; Leong, Chee-Onn; Stocks, Michael; Kellam, Barrie; Marlow, Maria; Bradshaw, Tracey D.; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6891 – 6899;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1003-99-2, A common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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.

2-Bromo-5-fluoro-aniline (5.00 g, 95 mass percent article, 25.0 mmol), m-nitrobenzenesulfonic acid (2.65 g, 13.0 mmol), 20.0 mL of 85 wtpercent aqueous phosphoric acid solution and ferrous sulfate heptahydrate (65.5 mg, 0.250 mmol) were placed in a 100 mL three-neck flask equipped with a magnetic stirrer, a reflux condenser, a thermometer and a dropping funnel and the mixture was heated to 80¡ãC in an oil bath. Subsequently, trans-2-hexenal (6.51 g, 98 mass percent article, 65.0 mmol) was added dropwise thereto through the dropping funnel for 1 hour. After completion of the dropwise addition, the mixture was heated and stirred at 100¡ãC for 2 hours. Then, the reaction mixture was poured into water and neutralized to pH 7 by ammonia water. The neutralized liquid was extracted with dichloromethane, and then dichloromethane was removed under reduced pressure. The resulting crude reaction product was purified by column chromatography (Hexane/AcOEt=100/0->1/10) using silica gel, followed by drying under reduced pressure to give 625 mg of 8-bromo-5-fluoro-2-propylquinoline as a yellowish white solid (yield: 9.33percent). 1H-NMR (300 MHz, CDCl3) delta: 8.32 (d, 1H), 7.95-7.90 (m, 1H), 7.40 (d, 1H), 7.08-7.01 (m, 1H), 3.05-3.00 (m, 2H), 1.95-1.85 (m, 2H), 1.05 (t, 3H) [MS] EI (m/z): 268 (M+), CI (m/z): 269 (MH+)

The synthetic route of 1003-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP1847545; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-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. Computed Properties of C6H5BrFN

To a stirred solution of 2-bromo-5-fluoroaniline (3.0 g, 15.95 mmol) in dichloromethane (50 mL)was added di isopropyl ethylamine(5.5mL,31.9mmol)) followed by acetyl chloride (1.7mL,23.9 mmol) at 0 ¡ãC and starred at room temperature for 1 6h. The reaction mixture was washed with saturated sodium bicarbonate solution (50 mL), extracted the compound with dichloromethane, dried over sodium sulphate, filtered and concentrated. The crude product was purified on biotage with 6percent ethyl acetate/n- hexane as eluant to get desired product 142a as off white solid. (3.0 g, 96percent) . MS (ESI) m/z 233 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-99-2, its application will become more common.

Reference:
Patent; BIOIMICS AB; KIRSEBOM, Leif; UPADHAYAYA, Ram Shankar; KETHIRI, Raghava Reddy; VIRTANEN, Anders; (308 pag.)WO2017/222466; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-99-2, 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a 2-L reactor equipped with a mechanic agitator, a condenser, a thermocouple, a baffle, and nitrogen inlet were charged 228 g of water, 200 g of 2-bromo-5-fluoroaniline and 80 g of 4-nitrophenol. To this mixture was charged 96percent sulfuric acid in 10-30 min at 20-120¡ã C. The mixture was heated to 135-140¡ã C. and 194 g of glycerol was charged into the reactor over two hours at 135-145¡ã C. The mixture was held at 135-145¡ã C. for 1 hour after the addition. The reaction mixture was cooled to below 20-50¡ã C. and slowly transferred to a 5-L reactor containing 1100 g of water and 1210 g of toluene. The 2-L reactor was washed with 300 g of water and the wash was combined into the 5-L reactor. The pH of the contents in the 5-L reactor was adjusted to pH 8-10 by adding approximately 1233 g (1370 mL) ammonium hydroxide (28-30percent NH3) at 20-40¡ã C. The mixture was stirred at room temperature for 15 min and the solid by-product was filtered off while the filtrate was retained. The filter cake was washed with 400 ml of toluene and the all the filtrate was combined and charged a 3-L reactor. About 500 ml of 8.5percent KOH solution was charged into the 3-L reactor and stirred for 10 min and bottom aqueous layer was spit off. A second portion of 500 ml of 8.5percent KOH solution was added and the mixture was stirred for 15 min and the bottom aqueous layer was split off. Water 500 ml was added and stirred for 15 min before the bottom aqueous layer was split off. The organic layer was heated to distill off about 100-200 ml of toluene to azeotropically remove water. A clear solution will be obtained. Typical yield 178 g real 8-bromo-5-fluoroquinoline, 75percent.Alternatively, 8-bromo-5-fluoroquinoline was prepared by adding a warm mixture containing 2-bromo-5-fluoroaniline (100 g, 1.0 eq), 4-nitrophenol (40 g, 0.54 eq), and glycerol (97 g, 2.0 eq) over 1.5 hours to sulfuric acid (267 ml) and water (114 mL) at 140-150¡ã C. The initial mixture showed 37.8percent 4-nitrophenol by relative HPLC area percent. Samples showed 4.7percent 4-nitrophenol immediately after adding 50percent of mixed starting materials and 5.0percent immediately after adding all of the materials. The yield upon workup was 87.5percent, with total impurities 0.29percent. Addition of less (0.46 eq, 34 g) 4-nitrophenol also successfully produced the intermediate of interest at acceptable yield.

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; Wyeth; US2007/27160; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary