Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 399-94-0, name is 1-Bromo-2,5-difluorobenzene, 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 399-94-0, name: 1-Bromo-2,5-difluorobenzene

General procedure: To an oven-dried 25 mL Schlenk tube containing a stirring bar was added 4.5 mg Pd(OAc)2 (0.02 mmol), 15.7mg nBuPAd2 (0.44 mmol), 2-bromofluorobenzene (0.50 mmol), salicylaldehyde (0.50 mmol), potassium carbonate (1.0 mmol). The Schlenk tube was vacuumed and then purged with argon before DMF (2.0 mL) was injected using a syringe. Afterwards the Schlenk tube in the ice bath was degassed by evacuation and back fillingwith argon three times. The reaction mixture was then stirred for 12 h at 120 C. After the reaction was complete,the reaction mixture was diluted with water (5 mL), extracted with ethyl acetate (3 x 10 mL) and dried withanhydrous Na2SO4. After filtration and addition of silica gel into the solution, the organic solvent was reduced evaporated. The crude product was purified by column chromatography using ethyl acetate/n-pentane.

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:
Article; Shen, Chaoren; Wu, Xiao-Feng; Synlett; vol. 27; 8; (2016); p. 1269 – 1273;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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. HPLC of Formula: C6H3BrF2

To a clean and dry 72 L round bottom flask was added l-bromo-2,4-difluorobenzene (1586 g, (0373) 1.15 equiv, Oakwood lot H4460) and MTBE (20 L, 12.6 vol). This solution was cooled to – 70 to -75 °C and treated with n-BuLi (3286 mL, 1.15 equiv, 2.5 M in hexanes, SAFC lot 32799MJ), added as rapidly as possible while maintaining -75 to -55 °C. This addition typically required 35-45 minutes to complete. (NOTE: If the n-BuLi is added slowly, a white slurry will form and this typically gives poor results). After stirring at -70 to -65 °C for 45 minutes, a solution of compound 3-Br (2000 g, 1.0 equiv, AMRI lot 15CL049A) in MTBE (3 vol) was added rapidly (20-30 min) by addition funnel to the aryl lithium solution while maintaining -75 to -55 °C. After stirring for 30-60 minutes at -75 to -55 °C, the reaction was analyzed by GC/MS and showed only trace (0.5percent AUC) l-bromo-2,4-difluorobenzene present. The reaction was slowly quenched with aqueous 2 M HQ (3.6 L) and allowed to warm to room temperature. The mixture was adjusted to pH = 6.5 to 8.5 using NaHCC>3 (4 L), and the organic layer was separated. The MTBE layer was washed with brine (5percent NaCl in water, 4 L), dried over MgS04, filtered, and concentrated. In order to convert the intermediate hemi-acetal to 4, the crude mixture was heated inside the 20 L rotovap flask at 60-65 °C for 3 hours (under vacuum), at this point all the hemi-acetal was converted to the desired ketone 4- Br by *H NMR (CDC13). This provided crude compound 4-Br [2.36 kg, 75percent (AUC) by HPLC] as a brown oil that solidified upon standing. This material can then be used “as-is” in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 348-57-2, its application will become more common.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, Willam, J.; YATES, Christopher, M.; WO2015/143142; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 583-70-0, 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 583-70-0 as follows.

According to Scheme 1 Step i: To a solution of 1-bromo-2,4-dimethyl-benzene (20.00 g, 108.07 mmol, 1.00 eq) in THF (100 mL) under N2 atmosphere and cooled to -70C, was added n-BuLi (2.5 M, 45.39 mL, 1.05 eq) dropwise. The reaction mixture was stirred at -70C for 2 hr. Then a solution of 1,4-dioxa-spiro[4.5]decan-8-one (17.72 g, 113.47 mmol, 1.05 eq) in THF (100 mL) was added dropwise at -70C, the reaction mixture was stirred at -70C for 2 hr. The reaction mixture was quenched by water (300 mL) and extracted with EtOAc (200 mLx2). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silicagel (Petroleum ether/EtOAc 10/1 to 5/1). Intermediate 2a (24.00 g, 86.00 mmol, 79.57% yield) was obtained as a light yellow solid. 1H NMR (DMSO-d6; 400MHz) delta 7.31-7.29 (m, 1H), 6.90-6.89 (m, 2H), 4.66 (s, 1H), 3.87 (s, 4H), 2.49 (s, 3H), 2.21 (s, 3H), 2.00-1.94 (m, 4H), 1.79-1.76 (m, 2H), 1.53-1.51 (m, 2H).

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pragma Therapeutics; DUVEY, Guillaume; CELANIRE, Sylvain; (118 pag.)EP3459939; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2695-48-9, The chemical industry reduces the impact on the environment during synthesis 2695-48-9, name is 8-Bromo-1-octene, I believe this compound will play a more active role in future production and life.

Example 15(+>Pinanediol oct-7-ene- 1 -boronate In a freshly cleaned, flame dried, 2-neck flask equipped with a reflux condenser and charged with dry N2 gas was added Mg0 (1.4 g, 57 mmol, 1.1 eq) and anhydrous Et2O (20 rnL). To this mixture was added slowly dripped a solution of 8-bromooct-l-ene (10 g, 52.3 mmol) dissolved in dry Et2O (10 mL). After approx. 25% of the ethereal solution had been added the reaction was gently heated to reflux. The refluxing solvent was then kept refluxing by deliberate addition of the bromide solution. Upon completion the reaction was heated at reflux for 1 h, cooled to it, and added slowly to a -780C solution of trimethoxyborane (17.2 mL, 156 mmol, 3 eq) in diethyl ether. The reaction warmed to rt overnight and quenched by addition of a 10% H2SO4 solution (50 mL) and additional Et2O (60 mL). The biphasic solution was extracted with addition Et2O, washed with brine, dried over Na2SO4 and concentrated to approx Vi the original volume. To this was added (+)-pinanediol (8.94 g, 52.3 mmol, 1 eq) and after 2 h the solution was concentrated and purified by flash column chromatography (silica gel, eluted with 2% EtOAc in hexane) to afford (+)- pinanediol oct-7-ene-l-boronate (7.9 mg, 27.2 mmol, 52% yield) as a clear colorless oil.

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, 8-Bromo-1-octene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHENOMIX CORPORATION; WO2008/70733; (2008); A2;,
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 stirred solution of chloral hydrate (6.28 g, 37.97 mmol, CAS RN 302-17-0) in water (40 mL) was added Na2504 (43.73 g, 473.68 mmol, CAS RN 7757-82-6) at 25C and the reaction mixture was heated to 35C. Then a warmed mixture of 5-bromo-2-fluoro-phenylamine (6.5 g, 34.21 mmol, CAS RN 2924-09-6), water (40 mL) and concentrated HC1 (6.5 mL) followed by hydroxyl amine hydrochloride (8.08 g, 116.32 mmol, CAS RN 5470-11-1) in water (20 mL)were added to reaction mixture at 35C and reaction mixture was stirred at 90C for 3 h. After cooling to 25C the reaction mixture was filtered, dried and azeotroped with toluene to get the title compound as an off-white solid (7.6 g, 85%). MS (ESI): mlz = 263.1 [M-H].

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; (217 pag.)WO2017/137334; (2017); 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. 7051-34-5, name is (Bromomethyl)cyclopropane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: (Bromomethyl)cyclopropane

Preparation 4 2-Cvclopropylmethyl-ri,3″|dithiane-2-carboxylic acid ethyl esterTo 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 min. 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-MS: 247.0 (M+l).

According to the analysis of related databases, 7051-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/140183; (2007); 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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Product Details of 39478-78-9

5-bromo-2-methyl-4-nitroantine Two duplicate reactions were carried out in parallel: To a 3-necked 3 L flask was added H2SO4 (1.25 L). The flask was cooled to 0C. Then, 5-bromo-2-methylaniline (250 g, 1.34 mol) was added followed by the portion- wise addition of KNO3 (135.8 g, 1.34 mol). The solution was stirred at 20C for 3 hours. The crude reaction was then added to 10 L of ice water and a solid precipitated. The solid was filtered off to afford intermediate B.l, (5-bromo-2-methyl-4-nitroaniline after combining material from the duplicate reactions. The crude material was used directly for subsequent steps without additional purification.

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; MERCK SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
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 4117-09-3 as follows. Computed Properties of C7H13Br

A clean, dry, 1 L 3-neck flask equipped with a stir bar and nitrogen inlet was charged with magnesium turnings (10.31 g, 0.4241 mol, 1.5 equiv.) and ?0.1 mg of iodine, and the flask was purged with nitrogen for 5 minutes. 750 mL of anhydrous THF [15 mL/g of 7-bromohept-1-ene (3)] was charged and stirring was initiated. 7-Bromohept-1-ene (3, 50.02 g, 0.2824 mol, 1.0 equiv.) was slowly added drop wise over 10-15 minutes under nitrogen. During this period, the pink color of iodine disappeared during initial stages, the reaction was found to be slightly exothermic, and the temperature of the contents was raised from an initial ambient (20-23 C.) to about 31 C. After the addition was complete, the resulting pale gray color solution was cooled to room temp (23 C.) and stirring was continued for an additional 2.5 h under nitrogen to form the Grignard reagent (7-hept-1-ene magnesium bromide). Into a separate 2 L dry three neck RB flask equipped with a mechanical stirrer, thermocouple and an addition funnel with nitrogen inlet, diethyl oxalate (4, 82.61 g 0.5642 mol, 2.0 equiv.) and 750 mL of anhydrous THF [15 mL/g of 7-bromo-1-pentene (3)] were charged under nitrogen. The mixture was cooled to below -20 C. temperature (Jacket temperature: -23 C.) with stirring. The Grignard reagent (7-hept-1-ene magnesium bromide), which was prepared as described above, was transferred using a cannula into a side-arm addition funnel set on top of the 2 L RB flask. The reagent was added drop wise slowly into diethyl oxalate-THF solution over 1 h 50 min, while maintaining the jacket temperature below -23 C. During the addition of the Grignard reagent, the reaction was found to be exothermic and the internal temperature was raised to maximum of -18 C. After the addition was complete, the mixture was warmed to -15 C., and the progress of the reaction was monitored by HPLC. After 3 h at -15 C., the reaction mixture was warmed to -10 C., quenched with 3N hydrochloric acid solution and the final pH was adjusted to 1.4-1.6 by drop wise addition. During the quench, the internal temperature rose to -6.7 C. due to an exotherm while, the jacket temperature was maintained at -12 C. The mixture was stirred for an additional 10 min and the pH was re-checked and confirmed to be approximately, 1.7-1.8. The mixture was warmed to 22 C., and the pH was again re-checked (pH=2.8) and re-adjusted to pH=1.2 with 3N hydrochloric acid solution. A total of 81 mL of 3N hydrochloric acid solution was used for quench and pH adjustment. Agitation was stopped and the layers allowed to settle. The organic phase was separated, and the bottom aqueous layer was back-extracted with dichloromethane (1*100 mL). The combined organic phases were concentrated on a rotary evaporator (Bath temperature: 45 C./Vacuum) to give the crude product as a yellow oil. The crude product was dissolved in 200 mL of dichloromethane (some solids/salts were present) and 200 mL water. The bottom aqueous phase was separated and back-extracted with dichloromethane (2*200 mL). The combined organic phases were dried over anhydrous magnesium sulfate (25 g), filtered and concentrated on a rotary evaporator (bath temperature: 45 C., under vacuum), to afford a pale yellow viscous as oil. The crude product was purified by flash chromatography in four equal portions, with each portion dissolved in about 25 mL of dichloromethane for loading onto a silica gel column and eluted using 5-10% ethyl acetate in hexanes. The selected fractions were combined and concentrated on a rotary evaporator (bath temperature: 45 C., under vacuum), and further dried under vacuum (<5 mm/Hg) at ambient temperature for 4 h to afford 36.49 g of ethyl 2-oxonon-8-enoate (5) in 65.2% yield as colorless oil. According to the analysis of related databases, 4117-09-3, the application of this compound in the production field has become more and more popular. Reference:
Patent; AbbVie Inc.; Abrahamson, Michael J.; Pruyne, Julie J.; Kielbus, Angelica B.; Lallaman, John E.; Reddy, Rajarathnam E.; Chemburkar, Sanjay R.; (29 pag.)US10059969; (2018); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference 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.

To a solution of ethyl 9′-hydroxy-1 0′-methyl-2′-oxo-2′,7′-dihydrospiro[cyclobutane-1 ,6′-pyrido[2, 1-a]isoquinoline]-3′-carboxylate (90 mg, 0.265 mmol)in DMF (5 ml) was added K2C03 (73.2 mg, 0.530 mmol) and (bromomethyl)cyclopentane(51.8 mg, 0.318 mmol). The mixture was heated at 90 oc for 3 hours. The mixture wascooled to room temperature and partitioned between EtOAc and H20. The organic layerwas separated and the aqueous layer was extracted 2 times with EtOAc. The combinedorganic layers were washed brine, filtered, concentrated, and the residue purified by flashedchromatography (silica gel, 0-20 % MeOH in DCM to afford ethyl 9′-(cyclopentylmethoxy)-1 0′-methyl-2′-oxo-2′, 7′-dihydrospiro[cyclobutane-1 ,6′-pyrido[2, 1-a]isoquinoline]-3’carboxylate(60 mg, 53.7% yield). LCMS (ESI) m/z: 422.4 (M + 1t.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

10485-09-3, name is 2-Bromoindene, 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: 10485-09-3

Under an argon atmosphere, a solution of zinc chloride g, 28.0 mmol) in tetrahydrofuran suspension (5 mL) was added with a solution of isopropyl magnesium bromide in tetrahydrofuran (0.78 M, 30.7 mL) at 0 C., and the resultant was stirred at the same temperature for 1 hour. Then a solution of tetrakistriphenyl phosphine palladium (800 mg, 0.70 mmol) and 2-bromoindene (3.87 g, 20.0 mmol) in tetrahydrofuran (10 mL) was added thereto, and the resultant was further stirred at the same temperature for 16 hours. The reaction solution was added with a saturated aqueous solution of ammonium chloride, and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and the resultant residue was purified using silica-gel chromatography (hexane). 2-Isopropylindene (2.25 g, 71.1%) was obtained as a colorless oil.1H-NMR (400 MHz, CDCl3) delta; 1.22 (d, J=6.6 Hz, 6H), 2.77 (septet, J=6.6 Hz, 1H), 3.30 (s, 2H), 6.50 (s, 1H), 7.10-7.34 (m, 4H).

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOWA COMPANY, LTD.; US2010/22572; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary