Tag: M.W=100-200

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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

General procedure: Under N2 atmosphere, a mixture of intermediate 12 (263.5 mg,1.0 mmol), 3-bromoaniline (172.0 mg, 1.0 mmol), Cs2CO3 (325.8 mg,1.0 mmol), Pd2(dba)3 (45.8 mg, 0.05 mmol) and Davephos (31.5 mg,0.08 mmol) in MeCN (6.0 ml) was heated to reflux for 5 h. The reactionmixture was cooled to room temperature and diluted withethyl acetate. The resulting mixturewas filtered off and the solutionwas concentrated under vacuum to give a crude product 16 thatwas purified by column chromatography on silica using a solvent of10% ethyl acetate in hexanes. The desired compound 16 was obtainedas a yellow solid (220.0 mg, yield 72%). For the synthesis ofintermediate 13-15, compound 12 or commercially available 11and corresponding aromatic amine were used respectivelyfollowing the procedure described for 16.

The synthetic route of 39478-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Jiang; Zhang, Lanxi; Yan, Guoyi; Zhou, Peiting; Cao, Chaoguo; Zhou, Fei; Li, Xinghai; Chen, Yuanwei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 265 – 281;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 7073-94-1,Some common heterocyclic compound, 7073-94-1, name is 1-Bromo-2-isopropylbenzene, molecular formula is C9H11Br, 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.

General procedure: The bromobenzene (1 equiv) and (3-formylphenyl)boronic acid (1 equiv) were dissolved in a mixture of 1M sodium carbonate solution (15 mL), EtOH (5 mL) and toluene 15 mL). After nitrogen substitution, Pd(PPh3)4 (0.05 equiv) wasadded. The reaction mixture was stirred at 80 C under nitrogen atmosphere for 12 h. The reaction mixture was cooled, and wate r(15 mL) was added. The mixture was diluted with ethyl acetate(15 mL), and the insoluble material was filtered off through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography using a mixture of petroleum ether/ethyl acetate (10:1, v/v) as eluent to afford the desired product as a solid.

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-isopropylbenzene, its application will become more common.

Reference:
Article; Li; Liu, Chunxia; Yang, Jianyong; Zhou; Ye, Zhiwen; Feng; Yue, Na; Tong; Huang, Wenlong; Qian, Hai; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 608 – 622;,
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 626-88-0 as follows. category: bromides-buliding-blocks

Example 271 N-(1H-5-Indazolyl)-N-[1-(4-methylpentyl)-4-piperidyl]amine 4-Piperidone hydrochloride monohydrate (768 mg) and potassium carbonate (1.38 g) were dissolved in anhydrous N,N-dimethylformamide (10 ml), and 1-bromo-4-methylpentane (603 mg) was added dropwise to the solution at room temperature. The reaction solution was stirred at room temperature for 18 hr. Ethyl acetate was then added thereto, and the mixture was washed with water and saturated brine and was dried over anhydrous sodium sulfate. The organic layer was concentrated under the reduced pressure to give an intermediate. This intermediate (766 mg) was dissolved in titanium tetraisopropoxide (3.8 ml). 5-Aminoindazole (445 mg) was added to the solution, and the mixture was stirred at room temperature for 18 hr. Methanol (3.8 ml) and sodium borohydride (79 mg) were added to the reaction solution, and the mixture was stirred for 18 hr. The reaction solution was diluted with ethyl acetate (40 ml), and a minor amount of water was added thereto, and the mixture was then filtered under the reduced pressure. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel [chloroform/methanol] to give the title compound (200 mg, yield 13.3%). 1H-NMR (CDCl3, 400 MHz): 0.89 (d, J = 6.6 Hz, 6H), 1.15 – 1.26 (m, 2H), 1.49 – 1.59 (m, 5H), 2.07 – 2.23 (m, 1H), 2.35 – 2.39 (m, 2H), 2.90 – 3.00 (m, 2H), 3.29 – 3.38 (m, 1H), 6.80 – 6.82 (m, 2H), 7.26 (s, 1H), 7.88 (s, 1H) Mass spectrum (ESI-MS, m/z): 301 (M++1), 299 (M+-1)

According to the analysis of related databases, 626-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); 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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

In a 3 L four-necked flask purged with nitrogen, 148.3 g of 4-pentylphenylboronic acid, 102 g of 1-bromo-2,3-difluorobenzene, 5.56 g of tetrakistriphenylphosphine palladium (0) complex and 270 g of hydrogen carbonate Sodium and 750 ml of N, N-dimethylacetamide were added, and the mixture was stirred at 100 ° C. for 8 hours. The completion of the reaction was confirmed with a gas chromatograph (GC), and the system was cooled to room temperature. 1 L of water was added to the reaction system and stirring was carried out, 1 L of heptane was added thereto, and the mixture was vigorously stirred. The organic layer was separated and then extracted twice with 1 L of heptane. After washing the obtained heptane solution twice with 300 ml of water, the solvent was distilled off, and purification was carried out using 250 g of silica gel using heptane as a solvent, to obtain 100 g of the desired product as a colorless transparent liquid . Yield 72.8percent. GC purity 97.7percent. M + 260.

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; DIC CORPORATION; KUSUMOTO, TETSUO; AOKI, YOSHIO; (47 pag.)JP6136589; (2017); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

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

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

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

Some common heterocyclic compound, 2924-09-6, name is 5-Bromo-2-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. Product Details of 2924-09-6

To a solution of 5-bromo-2-fluoroaniline (5 g, 26.3 mmol) in DMF (30 mL) was added NCS (3.69 g, 27.6 mmol).The mixture was stirred at 60 C for 2 hr. The mixture was diluted with water, extracted with ethyl acetate twice. Then the organic layer was dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by CombiFlash, eluted with ethyl acetate in hexane (0-5%, 40 min), collected the desired fraction to afford the title compound (1 .2 g, 5.35 mmol, 20.32 % yield). 1 H NMR (400 MHz, DMSO-d6) delta 7.03 (dd, J = 10.8, 8.7 Hz, 1 H), 6.90 (dd, J = 8.8, 5.1 Hz, 1 H), 5.77 (s, 2H). LC-MS: [M+H]+ = 223.9,226.0,228.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2924-09-6, its application will become more common.

Reference:
Patent; NOVARTIS AG; DU-CUNY, Lei; XIAO, Qitao; XUN, Guoliang; ZHENG, Qiangang; (204 pag.)WO2018/234978; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary