Tag: M.W=100-200

Reference of 7051-34-5, 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. 7051-34-5, name is (Bromomethyl)cyclopropane, This compound has unique chemical properties. The synthetic route is as follows.

Dissolve M1 in THF Join K2CO3, bromomethyl cyclopropane stirring, the reaction solution was heated to reflux for 14 h. The reaction solution was cooled to room temperature, filtered, the solvent was distilled off under reduced pressure, and the residue was dissolved with dilute NaOH. The mixture was extracted with CH2Cl2, and the organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. 3-cyclopropylmethoxy-4-difluoromethoxy benzaldehyde M2.

The chemical industry reduces the impact on the environment during synthesis (Bromomethyl)cyclopropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guizhou Xinbang Pharmaceutical Co., Ltd.; Zhang Guanfu; (28 pag.)CN102964297; (2018); B;,
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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;,
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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;,
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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;,
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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., Application In Synthesis of 1-Bromo-2,3-difluorobenzene

Preparation 81 ,3-DICHLORO-2-(2,3-DIFLUOROPHENYL)PROPAN-2-OLTo a solution of 1-bromo-2,3-difluorobenzene (19.5 g, 0.10 mol) in dry diethyl30 ether (120 mL) at -780C, under nitrogen was added n-hexyl lithium (2.3 M in hexane, 41.7 ml, 0.096 mol) dropwise. The mixture was stirred for 1 min after which a solution of 1 ,3-dichloroacetone (12.2 g, 0.096 mol) in dry diethyl ether (30 mL) was added dropwise. The resulting mixture was stirred at -780C for 1 h and then brought to ambient temperature and stirred for 1 h. Aqueous hydrochloric acid (50 mL. 10percent) was35 added and the mixture was extracted with ethylacetate (2×50 ml). The combined organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane, 1 :9 to 1 :1 ) to give the title compound (1 1 .8 g, 48percent). MS m/z (rel. intensity, 7O eV) 241 (M+, 1 ), 193 (33), 191 (bp), 141 (1 1 ), 127 (68).

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; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; SONESSON, Clas; SWANSON, Lars; PETTERSSON, Fredrik; WO2010/58020; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 7051-34-5,Some common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, molecular formula is C4H7Br, 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.

Intermediate Preparation 7; 2-Cvclopropylmethyl-ri,3″|dithiane-2-carboxylic acid ethyl ester; To a flamed dried flask is added dry toluene (80 mL) and sodium hydride (60%, 33.5 mmol, 1.34 g). The reaction is cooled in a ice bath and a solution of ethyl 1,3 dithiane carboxylate (52 mmol, 10 g) and bromomethyl cyclopropane (62.4 mmol, 8.42 g) in DMF (24 mL) are added dropwise over 10 minutes. The ice bath is removed and the reaction is stirred for 18 h. Water is added (50 mL) and the organic layer is separated. The organic layer is washed with brine, dried (Na2SO4), and concentrated to a yellow oil (12 g, 92 %). LC-ES/MS: 247.0 (M+ 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopropane, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2009/12125; (2009); A1;,
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Synthetic Route of 5433-01-2, 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 5433-01-2 as follows.

To a solution of 1 -bromo-3-isopropylbenzene (10 g, 0.05 moi) in THF was added dropwise with BuLi (47 ml,, 0.075 niol) at -60 ‘C. After stirred 30 minutes, N-methoxy-N-methyiacetamide (6.22 g, 0.06 mol) was added. The mixture was stirred at -30C for 3 hours. Then the mixture was quenched with H20, the mixture was partitioned between EtOAc and water. The layer was separated and washed with water, brine, dried over Na2SC>4, and concentrated. The residue was purified by column chromatography to obtained the titled compound. ? NMR (CHLQRQFORM-d): delta 7.85 (s, i l l ). 7.79 (dt, j = 7.6, 1 .4 Hz, 1H), 7.33 – 7.53 (m, 2H), 3.00 (dt, J – 13.8, 6.9 Hz, 1H), 1.30 (d, J – 6.7 Hz, 6H)

According to the analysis of related databases, 5433-01-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RIPKA, Amy, S.; SAUNDERS, Jeffrey, O.; KAMENECKA, Theodore, Mark; GRIFFIN, Patrick, R.; WO2013/78233; (2013); A1;,
Bromide – Wikipedia,
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Application of 766-81-4, These common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, 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 catalyst [(IPr) AuCl] (3.1mg, 0.5mol%), 3- bromophenyl acetylene (1mmol), in methanol (1ml) and water (0.5ml) was added successively 25ml reactor.After the reaction mixture was reacted for 6 hours at 110 , cooled to room temperature.Rotary evaporation to remove the solvent, then purified by column chromatography (eluent: petroleum ether / ethyl acetate) to give pure title compound, yield: 93%

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; WANG, NANA; MA, JUAN; LI, FENG; (10 pag.)CN106032348; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, 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.

To a solution of 3-bromo-2-methylaniline (5 g,27 mmol) in chloroform (1 mL) was added acetic anhydride (5 g, 27 mmol) at 0 0C and the mixture was stirred at room temperature for 1 h. Potassium acetate (0.75 g, 7.8 mmol) and isoamyl nitrite (0.78 g, 58 mmol) were added and the reaction mixture was refluxed for 18 h. The volatiles were removed under reduced pressure and water (0.65 mL) was added. The mixture was concentrated, diluted with concentrated hydrochloride acid (1 mL) and heated at 50 0C for 2 h. After being cooled to room temperature, aqueous sodium hydroxide solution (50 %) was added until pEta=10. The aqueous mixture was extracted with ethyl acetate (100 mL><3). The combined organic layer was washed with brine (150 mL), dried over anhydrous sodium sulfate, filtered, evaporated and purified on silica gel column (3 % ethyl acetate in petroleum ether) to give the desired product (2.69 g, 34 % yield) as a solid. MS (ESI): m/z 197.0 [M+l]+. The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings. Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; ELSNER, Jan; HARRIS, Roy, L.; LEE, Branden; MORTENSEN, Deborah; PACKARD, Garrick; PAPA, Patrick; PERRIN-NINKOVIC, Sophie; RIGGS, Jennifer; SANKAR, Sabita; SAPIENZA, John; SHEVLIN, Graziella; TEHRANI, Lida; XU, Weiming; ZHAO, Jingjing; PARNES, Jason; MADAKAMUTIL Loui; FULTZ Kimberly; NARLA, Rama K.; WO2010/62571; (2010); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 2924-09-6, name is 5-Bromo-2-fluoroaniline, 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 2924-09-6, Computed Properties of C6H5BrFN

Example 25Synthesis of TRV 1 159TRV 1159 (4-(3-(benzylamino)-4-fluorophenyl)piperazin- 1 -yl)(phenyl)methanone [00164] Scheme for TRV 1 159[00165] 5-bromo-2-fluoroanile (0.500 g, 2.63 mmol) and benzaldehyde (0.27 mL, 2.63 mmol) were dissolved in DCM (8.8 mL) and then treated with NaBH(OAc)3 (0.837 g, 3.95 mmol) and AcOH (0.23 mL, 3.95 mmol). This mixture was stirred at room temperature under argon until complete by TLC. The reaction was quenched by the dropwise addition of IN NaOH (20 mL). This mixture was then extracted with EtOAc (3x 20 mL). The combined organic layers were washed with H2O, brine, dried (Na^SC^), filtered and concentrated to give 1.0 g of an oil. This crude oil was purified via flash chromatography (5 % EtOAc / hexane to give 0.6127 g (83 % yield) of the desired benzylamine. The benzyl amine (0.5032 g, 1.8 mmol), benzoylpiperazine hydrochloride (0.4897 g, 2.16 mmol) and NaOiBu (0.517 g, 5.38 mmol) were added to a tube. The tube was evacuated and flushed with argon for three cycles. Toluene (5.4 mL) and NMP (3.2 mL) were then added and the mixture was degassed with argon for 30 minutes. Pd2(dba)3 (0.033 g, 0.036 mmol) and BINAP (0.0448 g, 0.072 mmol) were then added, the tube was sealed and heated overnight at 100C. After cooling, the mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S0 . The material was filtered and concentrated under reduced pressure to give 1.3 g of crude brown oil. Initial purification via flash chromatography (45 % EtOAc / hexane) failed to separate the product from the minor by-product. A second chromatographic process (20 % EtOAc / hexane) was used to afford 0.1998 g (24 % yield) of TRV1159. NMR (500 MHz, CDC13) delta = 7.47-7.41 (m, 5H), 7.38-7.34 (m, 4H), 7.30-7.27 (m, 1H), 6.88 (dd, J = 1 1.5, 8.5 Hz, 1 H), 6.26 (dd, J = 7.5, 3.0 Hz, 1 H), 6.16 (dt, J = 8.5, 3.0 Hz, 1 H), 4.35 (s, 2H), 4.32 (br s, 1H), 3.89 (br s, 2H), 3.54 (br s, 2H), 3.09 (br s, 2H), 2.95 (br s, 2H). Example 26 Synthesis of TRV 1 158

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; YADAV, Arun; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2012/119035; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary