Category: 19932-85-5

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The crude product above (2.0mmol) was dissolved in DMF (20mL). The corresponding benzo[d]oxazol-2(3H)-one (2.4mmol) and Cs2CO3 (782mg, 2.4mmol) was added to the solution. The reaction mixture was stirred at 50C for 5h and then cooled to room temperature. The mixture was diluted with water (40mL) and then was extracted with ethyl acetate (20mL×3). The combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 11. White solid (35%, 4 steps). 1H NMR (300MHz, CDCl3) delta 8.64 (d, J=5.3Hz, 1H), 7.82 (d, J=9.2Hz, 1H), 7.37 (ddd, J=9.3, 5.7, 2.3Hz, 3H), 7.13-7.02 (m, 2H), 6.60 (t, J=5.7Hz, 1H), 4.49 (dd, J=9.0, 3.9Hz, 2H), 4.35 (t, J=5.0Hz, 2H), 3.92 (s, 3H). MS (ESI): 415.0, 417.1 [M+H]+. Purity: >95%

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

Reference：
Article; Lu, Dong; Shen, Aijun; Liu, Yang; Peng, Xia; Xing, Weiqiang; Ai, Jing; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 191 – 200;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5 its synthesis route is as follows.

To a deoxygenated mixture of tert-butyl ( (5- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2- yl) pyridin-2-yl) methyl) carbamate (62.5 mg, 0.187 mmol) , 6-bromobenzo oxazol-2 (3H) -one (40.0 mg, 0.187 mmol) , cesium carbonate (183 mg, 0.561 mmol) in DMF (0.93 mL) was added PdCl2(dppf) (21 mg, 0.028 mmol) and water (0.033 mL, 1.9 mmol) and the resulting mixture was heated at 140 for 30 min under microwave irradiation. The mixture was cooled and partitioned between EtOAc and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (0-5 MeOH in EtOAc) to afford the Boc protected intermediate. To a solution of this intermediate (18 mg, 0.053 mmol) in DCM (0.18 mL) was bubbled gaseous HCl for 1 min. The mixture was stirred for 1 h and then concentrated to afford the title compound. MS: m/z 242.24 (M + 1)

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; MERCK SHARP & DOHME CORP.; COOKE, Andrew J.; PITTS, Daniel; JOHNSON, Adam; BESHORE, Douglas C.; HURZY, Danielle; MITCHELL, Helen; FRALEY, Mark; MCCOMAS, Casey; SCHIRRIPA, Kathy; MERCER, Swati P.; NANDA, Kausik; MENG, Dongfang; WU, Jane; BABAOGLU, Kerim; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (156 pag.)WO2016/54807; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

Reference：
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 6-Bromobenzo[d]oxazol-2(3H)-one, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 19932-85-5, its synthesis route is as follows.

The bromo compound R (1.0 g, 4.67 mmol) was taken in an oven-dried RB equipped with magnetic stir-bar and dissolved in anhydrous THF (9 mL). The solution was cooled to -78 C. and MeMgBr (1.8 mL) was added slowly. The mixture was stirred for 45 min and anhydrous THF (37.5 mL) was added slowly to maintain the internal temperature at -50 C. After the solution was cooled back to -78 C., t-BuLi (10.6 mL, 9.8 mmol, 1.6 M in pentane) was added dropwise. Next, DMF (2.2 mL, 28.1 mmol) was added slowly to the yellow solution and the dry-ice bath was removed after 15 min. After 2 h, the reaction was quenched with water and the THF was removed under vacuo on a rotary evaporator. The residue was dissolved in ethyl acetate and washed with 1N HCl (5 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×5 mL). The organic layers were combined, dried over Na2SO4 and concentrated under vacuo on a rotary evaporator. The crude was first recrystallized from hexanes/ethyl acetate and then purified via gradient silica gel column chromatography using a mixture of hexanes and ethyl acetate (10:1 to 1:1) to obtain the desired aldehyde S as a white solid (500 mg, 66%). 1H NMR (500 MHz, CDCl3): delta 9.85 (s, 1H), 7.66 (dd, J=7.9 Hz, 1.2 Hz, 1H), 7.63 (s, 1H), 7.11 (d, J=7.9 Hz, 1H). 13C NMR (125 MHz, CDCl3): delta 190.9, 155.2, 144.1, 135.9, 131.4, 128.2, 109.6, 109.5

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; DUTTA, Aloke K.; US2014/309427; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.

To a solution of 1-bromo-4-chlorobutane (2.17?mL, 18.7?mmol), K2CO3 (3.87?g, 28.04?mmol) in ACN (1?mL) was added dropwise at a solution of 6-bromo-3H-1,3-benzoxazol-2-one (1) in ACN (3?mL). The mixture was heated at 80?C for 12?h. The inorganics were removed by filtration and the solvent was evaporated. The residue was purified by column chromatography (cyclohexane/ethyl acetate), 9:1 (v:v)) to afford 6-bromo-3-(4-chlorobutyl)-1,3-benzoxazol-2-one as a white solid (1.2?g, 3.94?mmol). Mp 61.9-62.4?C. 1H NMR (300?MHz, CDCl3): delta 7.39 (d, J?=?1.8?Hz, 1H), 7.34 (dd, J?=?8.3, 1.8?Hz, 1H), 6.88 (d, J?=?8.3?Hz, 1H), 3.87 (t, J?=?6.8?Hz, 2H), 3.60 (t, J?=?6.1?Hz, 2H), 2.27-1.74 (m, 4H). 13C NMR (75?MHz, CDCl3): delta 154.1, 143.1, 130.2, 126.9, 114.8, 113.8, 109.2, 77.5, 77.0, 76.6, 44.0, 41.6, 29.2, 25.0. LCMS m/z calc for [M + ACN + H]+: 345.6, 347.6, found: 345.1, 347.1.

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Article; Gay, Marion; Evrard, Caroline; Descamps, Florian; Carato, Pascal; Renault, Nicolas; Coevoet, Mathilde; Eddarkaoui, Sabiha; Baud, Catherine; Larchanche, Paul-Emmanuel; Buee, Luc; El Bakali, Jamal; Vingtdeux, Valerie; Sergeant, Nicolas; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 104 – 125;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 6-bromo-3H-1,3-benzoxazol-2-one 1 (5.00 g, 23.36 mmol) wassuspended in ACN (150 mL) and K2CO3 (9.69 g, 70.09 mmol) wasadded. The reaction mixture was stirred at 80 C for 30 min. 1-(2-Chloroethyl)piperidine hydrochloride (4.30 g, 23.36 mmol) or 3-chloropropylpiperidine hydrochloride (5.5 g, 28 mmol) was addedand the reaction mixture was stirred at 80 C for another 12 h. Theinorganics were removed by filtration and the solvent was evaporated.The residue was purified by flash chromatography (DCM/MeOH(NH3), 9.8:0.2 (v/v)) to afford compounds 2 and 3.4.1.3 6-Bromo-3-[2-(piperidin-1-yl)ethyl]-1,3-benzoxazol-2-one (2) Beige solid (7.58?g, 23.1?mmol, 99%). Mp 85.1-85.8?C. 1H NMR (300?MHz, CDCl3): delta 7.36 (d, J?=?1.8?Hz, 1H), 7.31 (dd, J?=?8.3, 1.8?Hz, 1H), 6.92 (d, J?=?8.3?Hz, 1H), 3.90 (t, J?=?6.6?Hz, 2H), 2.64 (t, J?=?6.6?Hz, 2H), 2.51-2.38 (m, 4H), 1.60-1.35 (m, 6H). 13C NMR (75?MHz, CDCl3): delta 154.1, 143.1, 130.7, 126.6, 114.4, 113.5, 109.9, 56.0, 54.7, 40.3, 26.0, 24.2. LCMS m/z calc for [M+H]+: 325.1, 327.1 found: 325.1, 327.1.

The chemical industry reduces the impact on the environment during synthesis,19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

Reference：
Article; Gay, Marion; Evrard, Caroline; Descamps, Florian; Carato, Pascal; Renault, Nicolas; Coevoet, Mathilde; Eddarkaoui, Sabiha; Baud, Catherine; Larchanche, Paul-Emmanuel; Buee, Luc; El Bakali, Jamal; Vingtdeux, Valerie; Sergeant, Nicolas; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 104 – 125;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5 its synthesis route is as follows.

A mixture of 6-bromo-1 ,3-benzoxazol-2(3H)-one (2 g ; 9.34 mmol) and copper (I ) cyan ide (1 .42 g; 1 5.86 mmol) in 6 m l D M F is heated at 1 50C u nder nitrogen atmosphere for 22 hr. After cooling to room temperature, a solution of 1 .55 g (31 .6 mmol) of sodium cyanide in 32 ml water is added followed by 1 hr stirring. The system is extracted thoroughly with ethyl acetate, washed with brine, dried and concentrated in vacuo to provide 1 .5 g (93 % yield) of the title compound enough pure as to prosecute the syntesis.

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; GUAL ROIG, Silvia; PRAT QUINONES, Maria; PUIG DURAN, Carlos; WO2013/68552; (2013); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5 its synthesis route is as follows.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.

Step 2: Bromide 1 (12.8 g, 59.6 mmol) was dissolved in anhydrous THF (220 mL), and the solution was cooled to ?78 C. Solutions of MeMgBr (21.9 mL of a 3.0 M solution in Et2O, 65.6 mmol), sec-BuLi (50.4 mL of a 1.3 M solution in cyclohexane, 65.6 mmol), and 1,4-Cyclohexanedione mono-ethylene ketal (11.2 g, 71.5 mmol) in anhydrous THF (10 mL) were added sequentially at 30-minute intervals. After the final addition, the reaction mixture was allowed to warm to room temperature. The reaction was quenched by the addition of 1N HCl (25 mL). The reaction mixture was diluted with EtOAc (500 mL), washed with saturated NaCl (250 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to provide a mixture of 2 and 3, as a brown oil.

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Nikam, Sham Shridhar; Scott, Ian Leslie; Sherer, Brian Alan; Wise, Lawrence David; US2003/236252; (2003); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.

Intermediate 13: 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carbonitrile To a solution of 6-bromo benzoxazolinone (2 g, 9.4 mmol) in DMF (20 mL) was added CuCN (16.79 g, 188 mmol), and the reaction was stirred at 175 C. for 6 h. The reaction progress was monitored by TLC (100% EtOAc). The reaction was diluted with EtOAc (10 mL) and filtered through Celite brand filter agent. The organic layer was concentrated and purified by column chromatography (silica gel, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 158.9 (MH-).

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; AMGEN INC.; BISWAS, Kaustav; CHEN, Jian J.; GORE, Vijay Keshav; HARRIED, Scott; HORNE, Daniel B.; KALLER, Matthew R.; MA, Vu Van; SHAM, Kelvin; ZHONG, Wenge; US2014/45855; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem