Tag: M.W=200-300

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. 58971-11-2, name is 3-Bromophenethylamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromophenethylamine

Weigh 0.382 g (2 mmol) of 3,5-dichlorosalicylaldehyde was dissolved in 30 mL of ethanol, 285 muL (2 mmol) of 3-bromophenethylamine was added dropwise and stirred under reflux for two hours. After cooling the system, 0.22 g (1 mmol) of zinc acetate dihydrate and 0.168 g (2 mmol) of sodium bicarbonate were added and the mixture was refluxed for two hours. The solution is cooled to produce a large amount of yellow precipitate.Filtered, rinsed three times with ethanol, and the precipitate was collected to give the crude product. The crude product was added to a tetrahydrofuran solution, dissolved by heating, and slowly precipitated a yellow solid at room temperature.Filtration gave product complex 2 (0.453 g, yield 55.9%).

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; Jilin University; Men, guangwen; (14 pag.)CN104262195; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13633-25-5, These common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, 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.

The reaction mixture of 28 (0.50 g, 1.5 mmol) and (4-bromobutyl)benzene (36) (0.34 ml, 2.0 mmol) in dry 1,4-dioxane (16 ml) was stirred for 4 days to afford the title compound as a white solid in 90% yield (0.66 g). mp: 224-225 C; 1H-NMR (400 MHz, DMSO-d6): delta = 7.19-7.39 (m, 15H), 6.76 (s, 1H), 5.20 (brs, 1H), 3.80 (m, 1H), 3.31-3.40 (m, 3H), 3.18 (m, 3H), 2.95 (m, 1H), 2.60 (m, 2H), 2.25 (brs, 1H), 1.55-1.91 (m, 8H); 13C-NMR (100 MHz, DMSO-d6): delta = 172.3, 143.0, 141.4, 128.3, 127.8, 127.7, 127.1, 127.0, 126.0, 80.7, 68.6, 66.3, 62.6, 59.3, 52.6, 34.4, 27.7, 20.8, 17.6; HRMS calcd. for C31H36N1O3 [M]+: 470.2695; found: m/z = 470.2691; HPLC (Method A): tR (min) = 9.15 (96%).

The synthetic route of 13633-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamashita, Yasunobu; Tanaka, Ken-ichiro; Yamakawa; Asano; Kanda, Yuki; Takafuji; Kawahara, Masahiro; Takenaga, Mitsuko; Fukunishi, Yoshifumi; Mizushima; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3339 – 3346;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 2051-99-2, 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. 2051-99-2 name is 1-Bromo-4-isobutylbenzene, 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.

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4¡Á10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.1 (S)-Ethyl 2-(4-isobutylphenyl)propanoate 7a Colorless oil, 89% yield, 88:12 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (0.5% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, major tr = 12.80 min (S), minor tr = 14.45 min (R)). [alpha]D20 = +33.9 (c 1.1, CHCl3). 1H NMR (300 MHz, CDCl3) delta: 7.21 (d, J = 8.1 Hz, 2H), 7.09 (d, J = 8.1 Hz, 2H), 4.18-4.06 (m, 2H), 3.68 (q, J = 7.1 Hz, 1H), 2.45 (d, J = 7.2 Hz, 2H), 1.89-1.80 (m, 1H), 1.48 (d, J = 7.2 Hz, 3H), 1.21 (t, J = 7.1 Hz, 3H), 0.90 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta: 174.7, 140.4, 137.9, 129.2, 127.1, 60.6, 45.2, 45.0, 30.1, 22.4, 18.6, 14.1. HRMS (APCI-TOF): calcd for C15H23O2 [M+H]+ 235.1698, found 235.1707.

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

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 113170-72-2, 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 113170-72-2 as follows.

Step A: 7-bromo-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-amine (1099) To a 25 mL microwave tube was added a solution of 3-bromo-5-(trifluoromethyl)benzene-1,2-diamine (0.510 g, 2.0 mmol) in 6 mL of methanol, followed by addition of cyanic bromide (0.254 g, 2.40 mmol) and 4 mL of water. The mixture was stirred for 16 hr. TLC showed most SM was converted. The reaction mixture was heated at 80 C. for 1 hr and no SM was left. The solvent was removed via rotavapor and the residue was purified via column chromatography (ISCO RediSep gold column, 40 g) using 0-10% MeOH/DCM as mobile phase to afford the title compound. LC-MS (M+H)+: 280.10

According to the analysis of related databases, 113170-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1337523-99-5, 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. 1337523-99-5, name is 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of amine (1.02 g, 4.5 mmol) in CH2Cl2(30 mL) was added Et3N (0.73 g, 7.22 mmol) and Boc2O (1.15 g, 5.29 mmol). The reaction solution was stirred at rt for 16 h and the mixture was concentrated in vacuo to afford a residue which was purified by silica gel chromatography (1.24 mg, yield 84%) to give a white solid. ESI-MS (M-56+H)+: 270.0.1H NMR (400 MHz, CDCl3) : 7.29-7.27 (m, 1H), 7.22-7.20 (m, 2H), 4.80-4.71 (m, 2H), 2.76-2.70 (m, 2H), 2.03-2.01 (m, 1H), 1.84-1.74 (m, 3H), 1.48 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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 67567-26-4, Safety of 4-Bromo-2,6-difluoroaniline

a) 2,6-DifIuoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline A solution of 4-bromo-2,6-difluoroaniline (2.50 g, 12.02 mmol, 1.0 eq), bis(pinacolato)diboron (3.36 g, 13.22 mmol, 1.1 eq), Pd(dppf)CI2 (150 mg, 0.18 mmol, 15 mol %) and potassium acetate (3.54 g, 36.06 mmol, 3.0 eq) in DMSO was heated at 80C under nitrogen for 90 minutes. The reaction mixture was partitioned between EtOAc (100 mL) and saturated aqueous bicarbonate (100 ml_). The organic layer was washed with brine (3 x 100 mL), dried over MgS04 and concentrated in vacuo to give a brown solid (3.0 g, 97%); H NMR (400 MHz, DMSO-d6) delta ppm 6.94-7.07 (m, 2H), 5.66 (s, 2H), 1.17-1.28 (m, 12H); m/z (ES+APCI)+: 256 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 129316-09-2, 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. 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-phenyl-3,5-dimethylpyrazole (2.0680 g, 12 mmol, 1.0 eq.) was added sequentially to a dry three-necked flask with a magnetic rotor.1,3-Dibromo-5-tert-butylbenzene (7.1513 g, 24 mmol, 98%, 2.0 eq.), cuprous iodide (0.2971 g, 1.56 mmol, 0.13 eq.),Potassium phosphate (5.0945g, 24mmol, 2.0 equivalents) and trans-N,N’-Dimethyl-1,2-cyclohexanediamine (0.4528 g, 3.12 mmol, 98%, 0.26 eq.).Nitrogen was purged three times, then dimethyl sulfoxide (18 mL) was added under nitrogen.The reaction vial was then placed in a 120 C oil bath.After stirring for 5 days, it was cooled to room temperature, filtered through Celite, and ethyl acetate (30 mL¡Á3) was washed thoroughly.The obtained filtrate was washed with brine (20 mL¡Á2), and then evaporated and evaporated.All organic phases were combined and dried over anhydrous sodium sulfate. Filtration, concentration, and purification of the crude product by flash chromatography on silica gel column chromatography(Eluent: petroleum ether / ethyl acetate = 30/1 to 15/1) Intermediate 5 was obtained as a pale yellow oil, 2.5293 g, yield 55%.

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, 1,3-Dibromo-5-(tert-butyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Dai Jianxin; Zhao Xiangdong; She Yuanbin; Chen Shaohai; (53 pag.)CN108424426; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1137142-58-5, 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 1137142-58-5 as follows.

General procedure A for the preparation of intermediates 4-8; 2-Bromo-imidazo[2,1-b][1 ,3,4]thiadiazole (1 eq) and the appropriate amine (e.g. cycloprapanemethyl amine) (4.5 eq) were stirred at 135C under microwave irradiation (200W) for 5 minutes. After cooling down to room temperature, the reaction mixture was diluted with dichloromethane and purified by flash chromatography (Biotage , silica, dichloromethane:methanol) to yield the desired product (e.g. cyclopropylmethyl-imidazobeta.i-bj? .S^thiadiazol-2-yl- amine). Intermediate 4 Cyclopropylmethyl-imidazo[2,1-b][1,3,4]thiadiazoI-2-yl-amineThe title compound was obtained in 89% yield.1H NMR (300 MHz, CDCI3): delta 7.27 (brs, 1 H), 7.21 (d, J = 1.3, 1 H), 6.83 (s, 1 H), 3.01 (dd, J = 5.1 , 6.9, 2H), 1.04 – 0.80 (m, 1 H), 0.43 – 0.28 (m, 2H), 0.13 – 0.05 (m, 2H). MS (ES+) m/z 195.10 (M+H)+ (MW: 194.26).

According to the analysis of related databases, 1137142-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 54962-75-3, 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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

CuI (190 mg, 1 mmol), 4-methyl-1H-imidazole (1.64 g, 20 mmol), Cs2CO3 (3.25 g, 10 mmol), 3-bromo-5- (trifluoromethyl) aniline 2.40 g, 10 mmol), 1- (5,6,7,8-tetrahydroquinoline-8-substituted) ethanone (350 mg, 2 mmol) was dissolved in DMF (30 mL), protected with argon, heated to 130 C., and reacted for 24 hours.After the reaction was completed, it was cooled to room temperature, spin-dried, and separated by silica gel column chromatography. The white solid obtained by recrystallization was the target product (1.7 g, yield: 71%)

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, 3-Bromo-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Sciences Guangzhou Bio-pharmaceutical And Health Institute; Ding Ke; Li Yupeng; Shen Mengjie; Long Huoyou; Zhang Zhang; Leng Fang; Lu Xiaoyun; (51 pag.)CN103539784; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 49764-63-8, These common heterocyclic compound, 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, 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.

General procedure: Triphenylstibane(35.5 mg, 0.1 mmol, 10 mol%) and diamine 2 (1.2 mmol) were added to a solution of -hydroxy ketone 1(1 mmol) in toluene (6 mL) under air. The solution was stirred at room temperature and monitored byTLC. The reaction mixture was concentrated under reduced pressure and the residue was purified bycolumn chromatography (CH2Cl2) on silica gel. The products were confirmed by comparison of mp,NMR data, and MS spectra with that in the literature. 822:

The synthetic route of 49764-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matsumura, Mio; Takada, Rie; Ukai, Yuu; Yamada, Mizuki; Murata, Yuki; Kakusawa, Naoki; Yasuike, Shuji; Heterocycles; vol. 93; 1; (2016); p. 75 – 83;,
Bromide – Wikipedia,
bromide – Wiktionary