Category: bromides-buliding-blocks

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,
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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 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

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

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

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

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

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

Reference of 57946-63-1,Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-bromo-4-(trifluoromethyl)benzenamine (1 g, 4.17 mmol, 1.00 equiv) in DMSO (20 mL), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.58 g, 6.22 mmol, 1.50 equiv), PdCl2(dppf) (91 mg, 0.12 mmol, 0.03 equiv), potassium acetate (1 g, 10.40 mmol, 2.57 equiv). The resulting solution was stirred overnight at 80¡ã C. in an oil bath. The resulting mixture was combined with the solution of the previous batch and then diluted with 100 mL of ethyl acetate. The resulting mixture was washed with 2*100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). This resulted in 1.2 g of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzenamine as a yellow solid.

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

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 39478-78-9, The chemical industry reduces the impact on the environment during synthesis 39478-78-9, name is 5-Bromo-2-methylaniline, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried Schlenk tube with the presence of magnetic stir bar which is Teflon-coated was charged with Pd(dba)2 (11.5 mg, 0.02 mmol, 2 mol%) and ligand L4 (8.4 mg, 0.02 mmol, 2 mol%). The flask was evacuated and backfilled with nitrogen (3 cycles). Pre-complexation of palladium and ligand was initiated by injecting freshly distilled dry dichloromethane (2.0 mL) and Et3N (0.1 mL) into the tube. The solution was stirred and warmed with hair drier till the solvent condensed on the tube wall. The solvent was removed under vacuum. Aryl bromide (1.0 mmol), KOt-Bu (0.25 mmol), and potassium hexacyanoferrate(II) trihydrate (0.23 mmol) were charged successively to the tube followed by another 3 evacuation-nitrogen refill cycles. Water (1.0 mL) and acetonitrile (1.0 mL) were used as a solvent mixture. The tube was immersed into a preheated 50 C oil bath for 24 hours. The reaction was quenched by cooling to ambient temperature and added with EtOAc and water. The organic supernatant was analyzed by GC. The organic layer was separated and the remained aqua medium was further extracted with EtOAc (10 mL ¡Á 3). The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (230-400 mesh). The pure fractions were collected, dried under vacuum, and followed by proton (1H) and carbon (13C) NMR characterization

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

Reference:
Article; Yeung, Pui Yee; Tsang, Chun Pui; Kwong, Fuk Yee; Tetrahedron Letters; vol. 52; 52; (2011); p. 7038 – 7041;,
Bromide – Wikipedia,
bromide – Wiktionary