Month: March 2021

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 452-74-4, A common heterocyclic compound, 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, molecular formula is C7H6BrF, 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 1Preparation of 4-bromo-3-fluorobenzyl bromide (III)A solution of 4-bromo-3-fluorotoluene (21.5 g, 0.114 moles) in acetonitrile (200 ml) is added with N-bromosuccinimide, (NBS; 21.2 g, 0.119 moles). The mixture is refluxed, added with dibenzoyl peroxide (1.4 g, 0.004 moles), refluxed for 3 hour, then cooled at room temperature, and extracted with water. The aqueous phase is discarded, and the organic phase is washed with brine, dried over sodium sulphate, and concentrated under vacuum to give an oil (27.1 g, 90% yield).

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; Chiesi Farmaceutici S.p.A.; US2011/39934; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1422-54-4, 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. 1422-54-4 name is 2-Bromo-6-fluorotoluene, 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.

00183] Active magnesium (10 mmol) was added in a RB containing dry TBF (10ml) and added a iittie iodine and stirred the reaction mixture and to this was added compound 1 (in 2 ml THFJsIowiy and stirred to generate the Grignard reagent. The reaction mixture was cooled to 0 “C and added compound 2 (in THF) drop wise and stirred the reaction mixture at it for 2h. After 2h the reaction mixture was quenched with saturated MH4CI soliition and extracted wit EtOAc. The organic layer washed with water, brine, dried over sodium sulphate and evaporated under reduced pressure to obtain compound 3,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-6-fluorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; KANDULA, mahesh; WO2013/24376; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, 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. Quality Control of 1-Bromo-2,4-difluorobenzene

1-Bromo-2,4-difluoro-5-nitrobenzene: To a 0¡ã C. mixture of 1-bromo-2,4-difluorobenzene (20.0 g; 11.7 mL; 0.100 mol) and H2SO4 (76.8 mL) was added HNO3 (68.0 mL) over 45 min at such a rate that the internal temperature was <7¡ã C. The resulting mixture was stirred for 1 h at 0¡ã C., poured into ice water (400 mL), stirred vigorously for 2-3 min and extracted with CH2Cl2 (400 mL). The organic layers were washed with brine (1.x.500 mL), dried over Na2SO4, filtered and evaporated to give the product as a yellow oil (23.5 g, 95percent). 1H NMR (CDCl3) delta 8.39 (t, J=7.2 Hz, 1H), 7.14 (ddd, J=0.3, 7.8, 9.9 Hz, 1H). The synthetic route of 1-Bromo-2,4-difluorobenzene has been constantly updated, and we look forward to future research findings. Reference:
Patent; Marzabadi, Mohammad R.; Chen, Chien-An; Jiang, Yu; Lu, Kai; Andersen, Kim; US2006/79522; (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. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-N1-methylbenzene-1,2-diamine

Step C: 7-Bromo-1-methylquinoxaline-2,3(1H,4H)-dione Under a protection of nitrogen, to 5-bromo-N-1-methylbenzene-1,2-diamine (7.7g, 38.3mmol) and triethylamine (9.69g, 95.75mmol) in 1,2-dichloroethane (80 mL) was added oxalyl chloride monoethyl ester (6.27g, 45.96mmol) at 0C. It was stirred at 25C for 2 hours. The temperature was raised to 60C for stirring for 3 hours. The reaction solution was filtered, and the filter cake was washed twice with water (20mL). The filter cake was dried to give the title compound. 1H NMR (400MHz, DMSO-d6) delta=12.07 (br. s., 1H), 7.51 (d, J=1.2 Hz, 1H), 7.33 (dd, J=1.6, 8.2 Hz, 1H), 7.07 (d, J=8.6 Hz, 1H), 3.47 (s, 3H).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; LIU, Shilan; LIANG, Guibai; WANG, Hongjian; ZHANG, Ming; CHEN, Shuhui; (93 pag.)EP3640247; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 4549-33-1, name is 1,9-Dibromononane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 4549-33-1

Preparation 55 (R)-4-(Biphenyl-2-ylcarbamoyloxy)-1-(9-bromononyl)-1-azoniabicyclo[3.2.1]octane Bromide To a stirred solution of the product of Preparation 54 (1.21 g, 3.76 mmol) and triethylamine (1.05 mL, 7.52 mmol) in acetonitrile (18.8 mL) was added 1,9-dibromononane (994 muL, 4.89 mmol) and the reaction mixture was heated at 50 C. for 4 h. The reaction mixture was then cooled and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and the organic layer was washed with saturated aqueous sodium bicarbonate (10 mL), dried (magnesium sulfate) and solvent removed under reduced pressure. The crude product was purified by flash chromatography (10% methanol/dichloromethane, 0.5% ammonium hydroxide) to give the title compound (1.04 g, 1.97 mmol, 52% yield).

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mammen, Mathai; Dunham, Sarah; US2005/113417; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 18392-81-9,Some common heterocyclic compound, 18392-81-9, name is 5,6-Dibromobenzo[c][1,2,5]thiadiazole, molecular formula is C6H2Br2N2S, 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.

1. 1 mmol of 5,6-dibromobenzothiadiazole,2 mmol of triphenylamine-4-boronic acid pinacol ester, 0.05 mmol of tetrakis(triphenylphosphine)palladium, 0.1 mmol of tetrabutylammonium bromide, 6 mmol of sodium hydroxide and 10 ml of toluene, reacted at 120 C for 48 h, with water Extract with dichloromethane and combine the organic layers.After drying, the organic solvent is removed, and purified by using a mixed solvent of dichloromethane and petroleum ether as a solvent column chromatography.4,4′-(Benzo[c][1,2,5]thiadiazole-5,6-diyl)bis(N,N-diphenylaniline) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dibromobenzo[c][1,2,5]thiadiazole, its application will become more common.

Reference:
Patent; Heilongjiang University; Han Chunmiao; Zhao Bingjie; Xu Hui; (30 pag.)CN110028506; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 76153-06-5, A common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

Isothiocyanatomethane (0.055 g, 0.746 mmol) in N,N-dimethylformamide (1.0 mL) was added dropwise slowly to a stirred solution of 5-bromo-3-methylbenzene-l,2-diamine (0.150 g, 0.746 mmol) in N,N-dimethylformamide (1.5 mL) at 0 0C. The cold bath was removed, the reaction mixture was capped and stirred at room temperature for 48 h. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.157 g, 0.821 mmol) was added and the reaction mixture capped and heated at 40 0C overnight. The resulting mixture was diluted with methanol, filtered and purified using reverse-phase preparatory HPLC (10-50 % acetonitrile + 0.1 % TFA in H2O + 0.1 % TFA, over 30 min). Fractions containing the desired product were combined and most of the solvent removed under reduced pressure. Acetonitrile was added and the resulting mixture loaded on a Strata ion exchange column. The column was washed successively with water, acetonitrile, methanol and 5 % ammonium hydroxide in methanol. The product eluted with the 5% ammonium hydroxide in methanol and was concentrated under reduced pressure and dried under high vacuum to give the desired product (0.128 g, 0.53 mmol, 72 % yield) as a slightly yellow waxy solid. MS (ESI) m/z 240 [M]+, 242 [M+2]+.

The synthetic route of 76153-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; ELSNER, Jan; HARRIS, Roy, L.; LEE, Branden; MORTENSEN, Deborah; PACKARD, Garrick; PAPA, Patrick; PERRIN-NINKOVIC, Sophie; RIGGS, Jennifer; SANKAR, Sabita; SAPIENZA, John; SHEVLIN, Graziella; TEHRANI, Lida; XU, Weiming; ZHAO, Jingjing; PARNES, Jason; MADAKAMUTIL Loui; FULTZ Kimberly; NARLA, Rama K.; WO2010/62571; (2010); 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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrFN

To a solution of 5-bromo-2-fluoroaniline (1 g, 5.26 mmol) in L/,L/?-dimethylformamide (10 ml), potassium iodide (2.18 g, 13.1 mmol), and sodium carbonate (1 .95 g, 18.4 mmol) were added and the reaction mixture was heated to 150 C. Then 1 -bromo-2-(2-bromoethoxy)ethane (1.34 g, 5.77 mmol) was added and heating was continued for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2 x 15 mL). The combined organic extracts were dried over Na2S04, filtered and concentrated under reduced pressure to yield the crude product. The crude material was purified by flash column chromatography using hexane/ ethyl acetate (80:20) to afford the title compound (0.8 g, 58%).1H-NMR (400 MHz, CDCI3) d = 7.03-7.04 (m, 2H), 6.90-6.92 (m, 1 H), 3.87-3.88 (m, 4H), 3.08-3.10 (m, 4H).

The synthetic route of 2924-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AC IMMUNE SA; NAMPALLY, Sreenivasachary; GABELLIERI, Emanuele; MOLETTE, Jerome; (0 pag.)WO2019/233883; (2019); 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. 452-62-0, name is 3-Bromo-4-fluorotoluene, A new synthetic method of this compound is introduced below., SDS of cas: 452-62-0

14a. (2-Fluoro-5methylphenyl)(6-(4-methylthiophenyl)(2H-benzo(d)1,3-dioxolen-5-yl))methan-1-ol To a solution of 3-bromo-4-fluorotoluene (0.7 mL, 5 mmol) in anhydrous THF (25 mL) at -78 C. under nitrogen atmosphere, a solution of t-BuLi in pentane (5.9 mL, 10 mmol) was added and the mixture stirred for 15 minutes. (color change observed). To this reaction mixture the product of Example 1b (1.34 g, 5 mmol), dissolved in anhydrous THF (20 mL), was added drop-wise and stirred at -78 C. for 15 minutes, then slowly allowed to warm to room temperature and stirred for 3 hours at room temperature. The reaction was then quenched with saturated aqueous ammonium chloride and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate was evaported under reduced pressure. Purification by flash column chromatography using 5% ethyl acetate in hexanes as the eluant gave the title compound as a white solid, (1.42 g, 74% yield), mp 110 C. 1H NMR (CDCl3, 300 MHz) delta 7.26-7.18 (m, 5H), 7.01-6.98 (m, 1H), 6.87 (s, 1H), 6.82-6.76 (s, 1H), 6.69 (s, 1H), 5.97 (s, 1H), 5.95 (s, 2H), 2.50 (s, 3H), 2.31 (s, 3H), 2.10 (s, 1H). 13C NMR (CDCl3, 75.45 MHz) delta 159.5, 156.3, 147.1, 146.8, 137.4, 137.3, 135.0, 133.4, 133.4, 130.2, 129.8, 129.3, 129.2, 128.0, 127.9, 126.2, 115.0, 114.8, 110.0, 107.5, 101.2, 67.2, 20.8, 15.8. LRMS (APIMS) m/z 782 (2M+NH4)+, 365 (M-OH)+.

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; Khanapure, Subhash P.; Garvey, David S.; Earl, Richard A.; Ezawa, Maiko; Fang, Xinqin; Gaston, Ricky D.; US2002/119977; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary