Author: Jessica.F

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. 64695-79-0, name is 2-Bromo-4,5-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-4,5-difluoroaniline

To a mixture of compound 47a (10 g, 48.08 mmol) and compound 47b (20.84 g, 57.69 mmol) in toluene (200 mL) was added Pd (PPh3) 4 (2.78 g, 2.4 mmol) in one portion under N 2. The resulting black mixture was stirred at 100C for 12 h under N 2. The reaction was cooled to 25C and then treated with 6N HCl (10 mL) with stirring at 25C for 1h. It was diluted with water (400 mL) and extracted with EtOAc (120 mL 3). The combined organic layers was washed with 20%KF solution (200 mL) and brine (100 mL) successively, dried over sodium sulfate and concentrated in vacuum to give the crude product, which was purified by column chromatography on silica gel (5%EtOAc in petroleum ether) to give compound 47c (4.2 g, 51% yield) as a yellow solid. LCMS: R t = 0.709 min in 5-95AB_220&254. lcm chromatography (MERCK RP18 2.5-2mm), MS (ESI) m/z=171.9 [M+H] +. 1H NMR: (400MHz, CDCl 3) delta 7.50 (dd, J=8.8 Hz, 11.2 Hz, 1H), 6.41 (dd, J=6.8 Hz, 12.0 Hz, 1H), 6.37-6.17 (m, 2H), 2.52 (s, 3H).

The synthetic route of 64695-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (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. 33884-43-4, name is 2-(2-Bromoethyl)-1,3-dioxane, A new synthetic method of this compound is introduced below., SDS of cas: 33884-43-4

Sodium hydroxide (3.46g, 1.3 eq) was taken up in water (2OmL) and stirred for about 30 minutes. Then 3-tert-butyl phenol (10.0 g, 66.6 mmol) was added and the resulting mixture was stirred at room temperature for 30 minutes. Next, 2-(2-bromoethyl)-[l,3] dioxane (9.9 mL, 1.1 eq) was added ant the resulting mixture was heated at reflux for 40 hours. The reaction mixture was cooled to room temperature and then added ethyl acetate (150 mL) and with stirring acetic acid was added to pH = 4, followed by dilution with water (100 mL) and ethyl acetate (150 mL). After partitioning, the layers were separated and then washed the organic layer with water (3X 10OmL) and the ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as a colorless oil (16.9Ig).

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; F. HOFFMANN-LA ROCHE AG; DEWDNEY, Nolan James; HAWLEY, Ronald Charles; KONDRU, Rama K.; LAI, Yingjie; LOU, Yan; WO2010/122038; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-52-6,Some common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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 4 Preparation of (3S)-methyl 3-(benzyloxycarbonyl amino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate 116.05 g trifluorobromobenzene and 400 ml tetrahydrofuran were added to a clean flask. The resulting mixture was cooled to -10 to -5 C., and then 864 ml (0.7 mol) methyl magnesium bromide was added thereto dropwisely. The mixture was stirred for 1 hour for use. 23.5 g (S)-methyl 3-(benzyloxycarbonylamino)-4-oxo n-butyrate was dissolved in 300 ml THF, and added dropwisely to the mixture mentioned above and kept at this temperature for 3 hours after completion of the addition. 400 ml solution of ammonium chloride was added dropwisely. Layers were separated. The aqueous layer was extracted with tetrahydrofuran (200 ml*2). The organic layer was dried and concentrated to get 31.4 g (3S)-methyl 3-(benzyloxycarbonylamino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate (yield: 78.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,4,5-trifluorobenzene, its application will become more common.

Reference:
Patent; Zhu, Guoliang; Zhang, Jian; Yang, Lljun; Yao, Qingdan; Ying, Jie; US2012/178957; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 65896-11-9, 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. 65896-11-9, name is 2-Bromo-6-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A Schlenk tube was charged with Oxone (0.398 g, 0.648mmol) and trifloroacetic acid (0.099 mL, 1.296 mmol) in anhydrous dioxane (2 mL) under argon. To this mixture was added 2-fluoroaniline (0.06 g, 0.54 mmol), and the reaction mixture was heated to 90 C under argon until starting material was consumed. As the reaction progressed, the color turned from lightred to dark red. The mixture was then cooled to room temperature and washed with a saturated aqueous sodium bicarbonate.The mixture was extracted with EtOAc (2 ¡Á 20 mL) and the combined organic layers were dried over Na2SO4. After filtering andremoval of the solvent under reduced pressure in vacuo, theresidue was purified by silica gel (100-200 mesh) column chromatography(hexane-EtOAc, 9:1), to afford a pale-brown solid(65%) of 2-hydroxy-N-trifluoroacetanilides from 2-fluoroaniline(2a).

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, 2-Bromo-6-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Venkateswarlu, Vunnam; Balgotra, Shilpi; Aravinda Kumar; Vishwakarma, Ram A.; Sawant, Sanghapal D.; Synlett; vol. 26; 9; (2015); p. 1258 – 1262;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 345965-54-0, name is 1-(4-Bromophenyl)cyclopropanamine, 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 345965-54-0, name: 1-(4-Bromophenyl)cyclopropanamine

tert-Butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate In a 100-mL round bottom flask, 1-(4-bromophenyl)cyclopropan-1-amine (1 g, 4.48 mmol, 1.00 equiv) and di-tert-butyl dicarbonate (3.1 g, 13.49 mmol, 3.01 equiv) were mixed in tetrahydrofuran (20 mL), to which was added a solution of sodium bicarbonate (5 g, 59.5 mmol, 13.29 equiv) in water (10 mL) at room temperature. The resulting solution was stirred overnight at room temperature. After the reaction was done, the reaction mixture was extracted with ethyl acetate (3*10 mL) and the organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (10% to 50% gradient) to afford tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate (1.47 g, 99%) as light yellow solid. MS: m/z=255.7 [M+H-56]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)cyclopropanamine, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-4-(trifluoromethyl)aniline

To a 100-mLround-bottom flask was placed a solution of 2-bromo-4-(trifluoromethyl)aniline (4.8 g,20.00mmol) in THF (20 mL) then DMAP (488 mg,3.99 mmol) and Boc2O (8.72 g) were added. The reaction was heated to reflux overnight then concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtOAc/petroleum ether (1:50) affording 7.9 g of the title compound as a white solid. 1H NMR (300 MHz,CDCl3): oe 7.89 (s,1H ),7.62-7.59 (d,J = 9.0 Hz,1H ),7.38-7.35 (d,J = 9.0 Hz,1H ),1.42 (s,9H).

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 57946-63-1.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1753-75-9, The chemical industry reduces the impact on the environment during synthesis 1753-75-9, name is 5-Bromobenzo[c][1,2,5]thiadiazole, I believe this compound will play a more active role in future production and life.

A vial was charged with Ih (7 mg, 2 mol %) and LiCl (67.0 mg, 1.6 mmol) as necessary followed by a stirbar under an inert atmosphere. The vial was then sealed with a septum and purged under an inert atmosphere after which DME (0.8 mL) was added and the suspension was stirred until 1 h had dissolved. After this time, the organohalide (0.5 mmol) and the organomagnesium (0.8 mL, 1.0 M in THF or ether, 0.8 mmol) were added (active catalyst is indicated by the reaction solution turning orange). The septum was replaced with a Teflon-lined screw cap under an inert atmosphere and the reaction stirred at RT or warmed to 60 or 70 C. until complete. After this time, the mixture was diluted with a suitable organic solvent (15 mL) and washed successively with 1 M Na3EDTA solution (prepared from EDTA and 3 equiv of NaOH), water and brine. After drying (anhydrous MgSO4) the solution was filtered, the solvent removed in vacuo, and the residue purified by flash chromatography. A summary of the substrate scope that was explored is presented in Table 8.

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, 5-Bromobenzo[c][1,2,5]thiadiazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Total Synthesis, Ltd.; US2007/73055; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 3814-30-0, A common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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.

1. A solution of (bromomethyl)cyclopentane (1.8 g, 11.0 mmol) in THF (11 mL) was added dropwise to a suspension of Mg (528 mg, 22.0 mmol) and I2 (55.8 mg, 0.22 mmol) in THF (3 mL) at 75oC. The mixture was stirred at 75oC for 1 hr. A mixture of (cyclopentylmethyl)magnesium bromide (11.1 mL, 11.1 mmol, 1M in THF) was slowly added to a solution of S-500-6-1_1 (800 mg, 2.23 mmol) in THF (30 mL) at 15oC. After addition, the mixture was stirred at 15oC for 1 hr. The mixture was quenched with sat. NH4Cl (40 mL) and extracted with EtOAc (3 x 20 mL). The combined organic phase was washed with brine (2 x 30 mL), dried over Na2SO4, filtered and concentrated and purified by combi-flash (0-15% of EtOAc in PE) to give 100 (350 mg, 35%) as a solid. 1H NMR (400 MHz, CDCl3) delta 5.32-5.26 (m, 1H), 3.77-3.69 (m, 1H), 2.41-2.31 (m, 1H), 2.09- 1.89 (m, 4H), 1.88-1.69 (m, 4H), 1.68-1.55 (m, 6H), 1.54-1.27 (m, 12H), 1.26-1.15 (m, 2H), 1.14-1.05 (m, 4H), 1.04-0.99 (m, 5H), 0.98-0.88 (m, 4H), 0.87-0.81 (m, 3H), 0.69 (s, 3H). LCMS Rt = 5.661 min in 7.0 min chromatography, 30-90AB_E, purity 100%, MS ESI calcd. for C30H47 [M+H-2H2O]+ 407, found 407.

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; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; GRIFFIN, Andrew; LA, Daniel; (299 pag.)WO2018/75698; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 955959-84-9

In a stream of argon, 5.9 g of acetamide, 32.3 g of the intermediate 3 , 2.70 g of copper iodide, 40.8 g of potassium carbonate, 6.3 g of N’N-dimethylethylenediamine, and 300 mL of xylene were loaded, and then the mixture was subjected to a reaction at 175¡ãC for 19 hours. Further, 38.5 g of the intermediate 1 were loaded into the resultant, and then the mixture was subjected to a reaction at 175¡ãC for 19 hours. After the resultant had been cooled, water was added so that the resultant was filtrated. The residue was washed with acetone, methanol, and water three times each. Thus, 28.4 g of an acetamide body of the intermediate 13 were obtained. 28.4 g of the acetamide body of the intermediate 13, 26.3 g of potassium hydroxide, 25 mL of water, and 40 mL of xylene were loaded, and then the mixture was subjected to a reaction at 175¡ãC for 5 hours. After the resultant had been cooled, water was added so that the resultant was filtrated. The residue was washed with acetone, methanol, and water three times each, and was then purified with a short column (developing solvent: toluene). The resultant solid was washed with n-hexane and dried under reduced pressure. Thus, 16.6 g of a white solidwere obtained. The white solidwas identified as the intermediate 13 by FD-MS analysis.

The synthetic route of 955959-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2502908; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 25462-61-7, 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. 25462-61-7, name is 2,5-Dibromobenzene-1,4-diamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a Schienk flask, 2,5-dibromo-1,4-phenylenediamine (1 g, 3.76 mmol) and 2-(4,4,5,5-Tetramethyl-1,3,2-dioXaborolan-2-yl)-5-propylthiophene 10 (3.8 g, 15.04 mmol) were charged under the protection of nitrogen. After adding 75 ml toluene, 30 ml ethanol and 20 ml Cs2CO3 aqueous solution (2.0 mol/l), the mixture was degassed for 45 mm. Pd(PPh3)4 (435 mg, 0.376 mmol) was added. The mixture was thenheated to 80 C, stirred overnight, poured into brine and extracted by dichloromethane for several times. The organic phase was dried over Mg2SO4 and the solvent was evaporated in vacuo. The product was purified by chromatography on silica gel (CH2CI2) to give product 11 as yellow flaky crystal (860 mg, 63%). ?H NMR (400 MHz, CDCl3,. ppm): 1.00 (t, J 7.34 Hz, 6H), 1.73 (dd, .1= 15.00, 7.44 Hz, 4H), 2.80 (t, J = 7.36 Hz, 4H), 4.27-3.02 (br, 2H), 6.76 (m, 4H),7.02 (d, J = 1.96 Hz, 2H). 13C NMR (100 MHz, CDCl3, ppm): 145.9, 138.4, 136.2,125.8, 124.8, 121.9, 118.5, 32.4, 25.1, 14.0.

The synthetic route of 2,5-Dibromobenzene-1,4-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; ZHANG, Fan; WANG, Xinyang; TANG, Ruizhi; FU, Yubin; ZHUANG, Xiaodong; FENG, Xinliang; WU, Dongqing; WO2015/43722; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary