Category: 656-64-4

Reference of 656-64-4, These common heterocyclic compound, 656-64-4, name is 3-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.

General procedure: (Z)-N-(3-Bromo-4-fluorophenyl )-N’-hydroxy-1H-indazole-7-carboximidamide (8a). To a solution of 7 (25 mg,0.105 mmol) in THF (1 mL) at 60 C was 3-bromo-4-fluoroaniline (20 L, 0.105 mmol) was added andstirred for 10 min. A solution of NaHCO3 (13 mg, 0.157 mmol) in water (1 mL) was added dropwiseand stirred at 60 C for 3 h. The mixture was extracted with EA and washed with brine. The organic layer was dried over MgSO4 and concentrated to obtain the crude mixture which was purified bycolumn chromatography (MPLC) to give compound 8a.

Statistics shows that 3-Bromo-4-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 656-64-4.

Reference:
Article; Lee, Dong-Ho; Lee, Joo-Youn; Jeong, Jieun; Kim, Miok; Lee, Kyung Won; Jang, Eunseo; Ahn, Sunjoo; Lee, Chang Hoon; Hwang, Jong Yeon; Molecules; vol. 22; 11; (2017);,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products 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.

Compound 3 (80g, 0.4923mo1), compound 4 (280g, 1.474 mol) and ethanol (2.4L) were added into the reactor, then the reactor was heated to reflux for 1 hours, then the mixture was concentrated, and the crude product was washed with n-hexane/ethyl acetate (200mL, V/V=10: 1) , filtered, dried to obtain compound 5(138g, yield 88.7%).MS: 316 [M+lfb. ?H-NMR(400Hz, DMSO-d6): 11.42 (s, 1 H), 8.86 (s, 1 H), 7.17 (dd, 1 H), 7.08 (dd, 1H), 6.77 – 6.71 (m, 1 H), 6.24 (s, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; XU, Yong; HUANG, Lu; (26 pag.)WO2017/124822; (2017); 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.

Step C: 4-Amino-N-(3-bromo-4-fluorophenyl)-N’-hydroxy-1,2,5-oxadiazole-3-carboximidamide (4) 4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (33.8 g, 208 mmol) was mixed with water (300 mL). At 60 C., 3-bromo-4-fluoroaniline (Sigma-Aldrich) (43.6 g, 229 mmol, 1.1 equiv.) was added to the suspension with stirring for 10 min. A solution of sodium bicarbonate (26.3 g, 313 mmol, 1.5 equiv.) in water (300 mL) was added over 15 min with stirring at 60 C. After stirring 20 min, LCMS indicated reaction completion. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate (2*300 mL). The combined ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to give the desired product (65 g, 99%) as an off-white solid, which was used in the subsequent reaction without further purification. C9H7BrFN5O2 (MW 316.09), LCMS (EI) m/e 316/318 (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 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Tao, Ming; Frietze, William; Meloni, David J.; Weng, Lingkai; Zhou, Jiacheng; Pan, Yongchun; US2015/133674; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference 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.

The compounds BB-1-4 (1.00 g, 5.26 mmol, 1.00 eq), BB-18-1 (587.38 mg, 6.84 mmol, 1.30 eq), potassium phosphate (3.91 g, 18.41 mmol, 3.50 eq), triphenylphosphine (137.96 mg, 526.00 umol, 0.10 eq), and palladium acetate (59.05 mg, 263.00 umol, 0.05 eq) were dissolved in toluene (24.00 mL) and water (2.00 mL), heated to 100 C. in nitrogen ambient and reacted for 16 hours. After being heated, the reaction solution gradually turned dark brown from brown. Complete reaction of raw materials was observed by LCMS monitoring and a target compound was generated. The reaction solution was cooled to 23 C., followed by addition of 20 mL of water, extraction with ethyl acetate (20 mL*3), drying over anhydrous sodium sulfate, and filtration. A filtrate was dried by rotary evaporation under reduced-pressure distillation, and purified by flash silica gel column chromatography (petroleum ether:ethyl acetate=10:1). The reaction succeeded, and a yellow liquid product BB-18 (790.00 mg, yield: 99.35%) was obtained. MS (ESI) m/z: 152 [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 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; SHANDONG LUYE PHARMACEUTICAL CO., LTD.; ZHANG, Yang; FU, Zhifei; LUO, Miaorong; LI, Jian; CHEN, Shuhui; (93 pag.)US2019/169140; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application 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 solution of 3-bromo-4-fluoroaniline ( 1.000 g, 5.263 mmol), methyl 4-(bi momethyl)-3-fluoi benzoate ( 1.430 g, 5.789 mmol) and potassium carbonate ( 1.455 g, 10.525 mmol) in acetonitrile ( 10 mL) was stirred at the room temperature for 15 hr, filtered to remove solids, and concentrated under the reduced pressure to remove the solvents. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / hexane = 0 % to 10 %) to give methyl 4-(((3-bromo-4-fluorophenyl)amino)methyl)-3-fluorobenzoate as palw brown oil ( 1.104 g, 58.9 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 656-64-4, 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. 656-64-4, name is 3-Bromo-4-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 7. 2′,6-Difluoro-5′-(5-(2-hvdroxypropan-2-yl -lH-benzor(ilimidazoll- yl)biphenyl-2-carbonitrile (Compound 111).Scheme 18. Preparation of Compound 111.[168] Step 1. l-(4-(3-Bromo-4-fluorophenylaminoV3-nitrophenyl ethanone (31): 30 (5 g, 27.3 mmol) was mixed with 3-bromo-4-fluoroaniline (8.3 g, 44 mmol) in NMP (20 mL) and heated at 90 C. After 3 days the reaction was cooled and the mixture was poured into ice water (500 mL). The orange solid was filtered, washed with water (200 mL) and then washed with heptanes (100 mL). After drying under vacuum for 6 hours at 50 C, 11.2 g (>100%) of 31 was obtained. The sample contained residual NMP by NMR and was used directly in the next step.

The synthetic route of 3-Bromo-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONCERT PHARMACEUTICALS, INC.; LIU, Julie, F.; HARBESON, Scott, L.; WO2011/47315; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application 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.

Example 195 4-[(3-Bromo-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile A mixture of 3.8g (16.33mmol) of 4-chloro-6-nitro-3-quinolinecarbonitrile and 3.7g (20mmol) of 3-bromo-4-fluoroaniline in 200mL of ethanol was refluxed for 3hr. After the solvent was removed, the residue as dissolved in ethyl acetate and washed with sodium bicarbonate. The product was collected as a pale yellow solid, 6.5g (71%); ESMS m/z 387.3, 389.2, mp 269-270C (dec).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; Wyeth Holdings Corporation; EP1263503; (2005); B1;,
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

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. 656-64-4, name is 3-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Product Details of 656-64-4

4-(6-Chloro-4-(ethoxycarbonyl)chroman-7- yloxy)benzoic acid (Preparation 1) (0.214 g, 0.569 mmol) was dissolved in 1,2- dichloroethane (2 ml) and a drop of DMF was added. To the mixture was added oxalyl chloride (2M in dichloromethane) (0.313 ml, 0.626 mmol). Gas evolution was observed. The mixture was stirred for 2 hours at ambient temperature. A solution of 3-bromo-4- fluoroaniline (0.113 g, 0.597 mmol) and triethylamine (0.158 ml, 1.138 mmol) in dichloromethane (1 ml) was added to the acid chloride solution. The mixture was stirred for 0.5 hour and the crude mixture was purified on silica gel (EtOAc in hexanes gradient) to provide 0.2656 g of the title compound as a white solid (85%).

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

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2009/158426; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application 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.

3-bromo-4-fluoroaniline (60 g, 315.6 mmol), acetonitrile (600 mL), water (600 mL), and concentrated hydrochloric acid (300 mL).The mixture was cooled to 0-5 C in an ice bath, and a solution of sodium nitrite (23.4 g, 316 mmol) in water (300 mL) was added dropwise, maintaining the system temperature at 0-5 C.After 1 hour of reaction, urea (3.6 g, 60 mmol) was added to quench excess sodium nitrite and stirred for 10 minutes.Sodium sulfide nonahydrate (100.8 g, 420 mmol), sulfur powder (13.2 g, 420 mmol), NaOH (17.4 g, 432 mmol), water (300 mL) were sequentially added to a 1 L three-necked flask. The oil bath was heated to 75 C for 1 hour until the solution became clear. The clear solution was cooled to room temperature and added dropwise to the above reaction liquid, and the temperature of the system was maintained at 0 to 5 C. After the completion of the dropwise addition, the reaction mixture was extracted with ethyl acetate (1L 2), filtered, dried over anhydrous sodium sulfate and evaporated to dryness to give the crude product of 1,2-bis(3-bromo-4-fluorophenyl)disulfane (42 g) , yellow oil, yield 64%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Ye Guozhong; Liu Lei; Bao Rudi; Wu Shenghua; Deng Haining; (130 pag.)CN110041253; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary