Category: bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, 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 51376-06-8, Quality Control of 5-Bromobenzo[c][1,2,5]oxadiazole

5-Bromo-2,1,3-benzoxadiazole (10 g, 50.3 mmol) was dissolved in toluene (300 ml) and added Lithium chloride (6.4 g, 150 mmol), Pd(Ph3P)4 (2.90 g, 2.50 mmol), and allyl tributyltin (19 ml, 60 mmol). The reaction mixture was degassed and refluxed under N2 for 3 hrs. It was cooled and poured into water then extracted with ethyl acetate. The organic layer was washed with brine 1x, dried and evaporated to dryness. The residue was chromatographed through 120g ISCO Redi-Sep columns and eluted with 0-10% ethyl acetate / hexane to yield 5-allyl-2,1,3-benzoxadiazole. 1H-NMR (500 MHz, DMSO): delta ppm 7.96 (d, J=9.1 Hz, 1H), 7.44(d, J= 9.1 Hz, 2H), 5.95-6.04 (m, 1H), 5.17 (d, J=14.7Hz, 1H), 5.15 (d, J=8.9Hz, 1H), 3.50 (d, J= 6.7Hz, 2H)

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]oxadiazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; TANG, Haifeng; PASTERNAK, Alexander; YANG, Lihu; WALSH, Shawn, P.; PIO, Barbara; SHAHRIPOUR, Aurash; TEUMELSAN, Nardos; (111 pag.)EP2632465; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 53078-85-6, 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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 36b (3.3 g, 17.7 mmol), glycerin (3.3 g, 35.5 mmol), nitrobenzene (2.2 g, 17.7 mmol) and 75% aqueous sulfuric acid (10 ml_, 138 mmol) is stirred at 1500C for 3 h (mixture turns black and viscous). The reaction mixture is cooled down, poured into 200 ml. ice-water and 10 N aqueous NaOH is added (30 ml_, 300 mmol). The black mixture is then shaken with 100 ml. EtOAc and is centrifuged in 50 ml_ portions. The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-centrifuged. All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes-EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62308; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, 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 17247-58-4, SDS of cas: 17247-58-4

Potassium ie tert-butoxide 1N in tetrahydrofuran (5.75 mL, 5.75 mmol) was added to a suspension of 5-bromo-2(1 H)-pyridone (1.00 g, 5.75 mmol) in dimethoxyethane (10 mL). After 30 minutes stirring at room temperature, potassium carbonate (0.56 g, 4.02 mmol) and (bromomethyl)cyclobutane (1 .29 mL, 1 1 .49 mmol) were added and the reaction mixture was refluxed for 24 hours. The resultant precipitate was filtered and rinced with ethyl acetate (20 mL). The filtrate was successively washed with water (20 mL) and brine (20 mL), then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate: 100/0 to 80/20) to provide 5-bromo-1 – (cyclobutylmethyl)-1 ,2-dihydropyridin-2-one (30a) ( 1 .10 g, 4.54 mmol, 79%). 1H NMR (400 MHz, CDCl3) delta 1.72-1.85 (m, 2H), 1 .85-1.97 (m, 2H), 2.01 -2.12 (m, 2H), 2.77 (septuplet, J = 7.5 Hz, 1 H), 3.92 (d, J = 7.5 Hz, 2H), 6.47 (d, J = 9.5 Hz, 1 H), 7.31 (dd, J = 2.7 Hz, J = 9.5 Hz, 1 H), 7.34 (d, J = 2.7 Hz, 1 H). MS m/z ([M+H]+) 242/244.

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

Reference:
Patent; LABORATOIRE BIODIM; BENAROUS, Richard; CHEVREUIL, Francis; LEDOUSSAL, Benoit; CHASSET, Sophie; LE STRAT, Frederic; WO2014/57103; (2014); 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. 418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 418762-26-2

To a stirred solution of 4-(2-(benzyloxy)ethoxy)-l-methyl-lH-pyrazole-5-carbonyl chloride (0.9 g, 3.05 mmol, 1 equiv) and 4-bromo-2-fluoro-5-methylaniline (0.6 g, 3.05 mmol, 1 equiv) in DCM was added Et3N (0.5 g, 4.58 mmol, 1.5 equiv) at 0 C under nitrogen atmosphere. The resulting solution was stirred for 30 min. The reaction was quenched with water at room temperature. The aqueous layer was extracted with CH2CI2 and the organic layer was concentrated under reduced pressure to give the title compound (1 g, 70.84%) as a white solid. LC-MS: (ES, m/z): [M+H]+ 462.

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; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary, Plake; DILLON, Michael, Patrick; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (248 pag.)WO2019/156987; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 185122-74-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 185122-74-1 as follows.

At 0 0C and under protective atmosphere, a solution of 2-propanesulfonyl chloride (1 1.87 mL, 121 mmol) in DCM (121 mL) was added gradually to a solution of 5-bromo-2,3- dihydro-7/-/-inden-1 -amine (12.8 g, 60.4 mmol) and 1 ,8-diazabicyclo[5.4.0]undec-7-ene (4.83 mL, 32.1 mmol) in dichloromethane (300 mL). The reaction was stirred at rt overnight. The reaction mixture was washed with 1 N KHSO4 (1x) and sat NaHCOs (2x) before being dried on IS^SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in hept) afforded the title compound as a white solid (6.0 g, 18.9 mmol, 31 %). MS (ESI) : m/z [M – H]”317.0.

According to the analysis of related databases, 185122-74-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); 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. 112279-72-8, name is 4-Bromo-2,3-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 112279-72-8

Benzyl chloroformate (1.1 mL, 7.5 mmol) was added dropwise with stirring to the Intermediate 52 (1.0 g, 4.8 mmol) in 10% aq. NaOH (15 mL)) and THF (30 mL) at ca. 0 C. The reaction mixture was stirred at r.t. for ca. 6 h. The reaction was quenched with 10% NH4Cl solution and extracted with DCM (2×50 mL). Combined organic layers were washed with brine, dried (Na2SO4), and concentrated under vacuum. The residue was purified by preparative TLC (10% ethyl acetate/petroleum ether) to give the product as a white solid. 1H NMR (400 MHz, CDCl3): 7.88 (m, 1H); 7.40 (m, 5H); 6.90 (m, 1H); 5.25 (s, 2H).

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; Gordeev, Mikhail Fedorovich; US2009/48305; (2009); 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1073-39-8

General procedure: In a 100 mL round-bottom flask, 1,2-dibromoethane (0.3 mL), magnesium (1.9 g, 80 mmol), and dry THF (5 mL) were added and stirred at ambient temperature for 30 min under nitrogen. Then 3-chloropropylmethyldichlorosilane (9.5 mL, 60 mmol) in THF(45 mL) was added dropwise over a period of 15 min and the reaction mixture was heated to 50 C for another 2 h. In another flask, magnesium (1.44 g, 60 mmol) and a grain of iodine were added. Then 4-bromobenzocyclobutene (9.15 g, 50 mmol) in 30 mL of dry THF was slowly added dropwise over a period of 2 h under nitrogen atmosphere. The reaction mixture was heated to 50 C and stirred continuously for 1 h. Resulted solution was added to the first flask. The reaction temperature was elevated to 50 C and kept overnight. Then the solution was poured into 1 M aq. HCl and extracted with hexane. The organic layer was washed twice with water and dried over anhydrous sodium sulfate. After removing the solvents by rotary evaporation, the residual oil was purified by silica-gel column chromatography (petroleum ether) to give the colorless oil (30.5 mmol, 5.74 g) in 61% yield.

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 1073-39-8.

Reference:
Article; Hu, Huan; Liu, Lili; Li, Zheng; Zhao, Cuijiao; Huang, Yawen; Chang, Guanjun; Yang, Junxiao; Polymer; vol. 66; (2015); p. 58 – 66;,
Bromide – Wikipedia,
bromide – Wiktionary

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16518-62-0 as follows. Safety of 3-Bromo-N,N-dimethylaniline

N,N-Diallyl-3-bromo-4-(2-bromo-4-(dimethylamino)benzyl)aniline (7) A solution of 3-bromo-N,N-dimethylaniline (7.54 g, 37.7 mmol) and 3-bromo-N,N-diallylaniline (9.51 g, 37.7 mmol) in glacial AcOH (250 mL) was treated with a 37 wt. percent solution of formaldehyde in H2O (30 mL). The resultant suspension was stirred at 80° C. for 2 h. After cooling to room temperature, the volatiles were removed under reduced pressure. The syrupy residue was dissolved in CH2Cl2 (100 mL), washed with sat. Na2CO3 (100 mL*2) and brine (100 mL), dried (Na2SO4), and concentrated under reduced pressure to afford a light brown syrup (16.9 g). 1H NMR analysis indicates that this mixture consists of approximately 30percent the desired product. The inseparable mixture was used in the subsequent step without further purification. 1H NMR (400 MHz, CDCl3): delta 6.91 (d, J=2.8 Hz, 2H), 6.82 (d, J=8.1 Hz, 2H), 6.55 (dd, J=2.8, 8.8 Hz, 2H), 5.78-5.87 (m, 2H), 5.14-5.20 (m, 4H), 3.98 (s, 2H), 3.85-3.87 (m, 4H), 3.15 (s, 6H).

According to the analysis of related databases, 16518-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHANG, Christopher J.; VAN DE BITTNER, Genevieve V.; HIRAYAMA, Tasuku; CHAN, Jefferson; US2014/51863; (2014); 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. 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, A new synthetic method of this compound is introduced below., COA of Formula: C4H10Br3N

To a mixture of 5-amino-3,4-dihydroquinolin-2(1H)-one 1(5.00 g, 30.83 mmol), bis(2-bromoethyl)amine hydrobromide(9.05 g, 33.91 mmol) and water (40 mL), a solution of potassiumhydroxide (1.90 g, 33.91 mmol,10 mL)was added dropwise at 80 C.Then the reaction mixture was stirred at 100 C for 3 h. The progressof the reaction was monitored by TLC. After the reaction wascompleted, the reaction mixture was cooled to the room temperature.The mixture was filtered and the filtrate was adjusted toPH 10 with the 10% aqueous solution of potassiumhydroxide. Theresultant solid was filtered, washed with water to afford 6.4 g of 5-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one 2 as a white solid.Yield 61%, m. p. 235e237 C; 1H NMR (300 MHz, DMSO-d6) d: 10.01(s, 1H, quinolin, eCONHe), 7.07 (t, J 7.9 Hz, 1H, quinolin-H7), 6.65(d, J 8.0 Hz, 1H, quinolin-H8), 6.58 (d, J 7.8 Hz, 1H, quinolin-H6),3.94 (s, 1H, NH), 2.82e2.94 (m, 4H, quinolin-H4 and eCH2-),2.67e2.84 (m, 6H, eCH2-), 2.35 (t, J 7.3 Hz, 2H, quinolin-H3); 13CNMR (75 MHz, DMSO-d6) d: 170.59, 150.18, 139.44, 127.33, 117.62,112.55, 110.18, 51.34, 46.73, 30.16, 20.38; LC-MS (ESI): m/z 232[MH].

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:
Article; Ji, Qinggang; Deng, Qiao; Li, Bing; Li, Baihui; Shen, Yangli; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 204 – 212;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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.

To a stirred solution of 4,5-diphenyl-2-((phenylsulfonyl)methyl)oxazole419 (2.7 g, 0.007 moles, 1.0 equiv) in dry THF (50 mL) was added potassium tert-butoxide (0.97 g, 0.003 mol, 1.2 equiv) under a nitrogen atmosphere at 0-5C and stirred was continued for 30 min. To this solution was added dropwise 8-bromo-1-octene (1.51 g, 0.008 mol, 1.1 equiv). After addition of the bromide, the reaction mixture was allowed to warm to room temperature and then stirred overnight. Water (30 mL) was then added to the reaction mixture followed by extraction with dichloromethane (2 x 25 mL). The organic layers were separated and combined, and the aqueous layer was washed with dichloromethane (2 x 10 mL). All the dichloromethane extracts were combined and dried over anhydrous sodium sulfate. Removal of the drying agent and concentration resulted in a reddish crude residue which was purified by column chromatography (hexane/ethyl acetate, 9:1) to give pure 4,5-diphenyl-2-(1-(phenylsulfonyl)non-8-en-1-yl)oxazole 20 (2.3 g, 66% yield) as athick colorless oil. Rf = 0.44 (hexane/ethyl acetate, 7.5:2.5); FT- IR: 3064, 2932, 2857, 1702, 1447, 1308, 1147, 686 cm-1; 1H NMR (400 MHz, CDCl3): delta 7.78-7.75 (m, 2H), 7.65-7.60 (m, 1H), 7.51-7.46 (m, 6H), 7.37-7.33 (m, 6H), 5.81-5.71 (m, 1H), 4.98-4.89 (m, 2H), 4.50 (dd, J = 10 Hz, 5.2 Hz, 1H), 2.40-2.34 (m, 2H), 2.03-1.98 (m, 2H), 1.40-1.31 (m, 8H) ppm; 13C NMR (175 MHz, CDCl3): delta 154.9, 147.0, 138.9, 137.3, 136.0, 134.0, 131.8, 129.1, 129.0, 128.9, 128.7, 128.5, 128.4, 128.2, 127.9, 126.6, 114.3, 65.9, 33.6, 28.8, 28.64, 28.58, 26.9, 26.4 ppm; HRMS calcd for C30H31NO3S (EI+) 485.2025, Found 485.2025

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-1-octene, its application will become more common.

Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Tetrahedron Letters; vol. 58; 13; (2017); p. 1280 – 1282;,
Bromide – Wikipedia,
bromide – Wiktionary